Accounting

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Bank Recs: Powering Through the Fog

New to bank reconciliations or unsure of the process? This session is designed just for you. We’ll break down what bank reconciliations are, why they’re essential for accurate financial reporting, and how to identify and fix common issues. Whether you’ve never completed a bank rec or just need a clearer understanding of the workflow, you’ll leave with the confidence and tools to handle reconciliations effectively.

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Cleared for Takeoff! Accurate Trust Reports

Trust reports are a vital part of your accounting toolkit. In this session, you’ll learn how to effectively review trust reports and dissect discrepancies with a problem-solving mindset. Whether you’re new to trust accounting or looking to sharpen your review process, this course will equip you with the skills to ensure accuracy and compliance in your trust reporting.

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Fees Made Easy: Elevate Your Revenue with Streamlined Strategies

Discover simple, effective ways to boost revenue through strategic fees. Learn how to implement and present fees that enhance your bottom line while keeping guests happy. Make fee management easy, transparent, and profitable.

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Flight School for Accounting

Buckle up as we take you through the fundamentals of accounting in property management. This session will cover key workflows, core concepts, and practical tips to help you confidently navigate your accounting system. Whether you’re just getting started or looking to sharpen your skills, we’ll help you soar to new heights.

Business Management

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From Landing to Lift-Off: Strategies for Guest Retention

Getting guests to book is just the beginning. Keeping them coming back is where the real growth happens. In this session, we’ll walk through practical ways to improve the guest experience from pre-arrival to post-stay using Streamline’s built-in tools. We’ll cover communication tips, loyalty opportunities, and automation strategies that help you build stronger guest relationships—and keep your bookings soaring.

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People-Powered Persuasion to Grow Your Rental Biz

In this competitive short-term rental market, standing out isn’t just about beautiful properties—it’s about understanding what truly drives decisions. In this dynamic session, we’ll explore how to apply proven principles of influence to help your business fly higher.

Property Care

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Housekeeping Standards: Elevating Property Care to New Heights

A Demo of Streamline’s Housekeeping and Maintenance Functionality

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No More Winging It! Taking Off with Property Care

Strap in as we guide you through setting up Property Care for smooth, high-flying success! Learn how to configure users, assign default roles, customize inspections, and unlock the newest features designed to streamline your workflow. Whether you’re launching a brand-new team or leveling up existing processes, this session will help you set the foundation for clear skies ahead.

Integrations

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Airbnb Jetpack: Boost Performance with Smart Tools

Take your operations to the next level with Airbnb Jetpack. Learn how to get the most from the Streamline + Airbnb integration, manage accounts, automate payments, streamline data, and use reporting tools effectively. Plus, get the latest updates and a look at what’s ahead.

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Expedition: Booking.com

All aboard for a Booking.com adventure! Whether you’re just setting sail or have already charted your course, this session will guide you through Streamline’s Booking.com integration. Discover how to connect, manage, and maximize your listings with confidence. It’s time to explore smoother connections, better bookings, and fewer headaches while making Booking.com your next great destination for travelers to book.

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Flying High with Airbnb

Fine-tune your Airbnb setup with key tools and strategies to streamline operations and enhance guest experiences. Learn how to manage taxes, pet fees, rates, reviews, and reservation changes all while getting a sneak peek at upcoming features built for flexibility and control.

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Soar To New Heights With StreamShare

StreamShare empowers Streamline Property Managers to rise above traditional booking methods by seamlessly sharing inventory with other Streamline Property Managers. In this session, you will learn how the Host-Agent model lets you diversify your portfolio, grow your online presence, and create a secondary source of revenue. StreamShare is your secret weapon for growing smarter, not harder.

General

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A Day in the Life With Streamline

Ever wondered how Streamline can support you through every twist and turn of a vacation rental manager’s day? From new reservations and guest communications to housekeeping issues, owner updates, work orders, and last-minute booking changes, this session follows a “day in the life” workflow, showing how to tackle it all efficiently in one system. Fast-paced, practical, and packed with real-world examples, this session will help you master daily operations with confidence. Whether you’re a hospitality pro, operations manager, salesperson, or all of the above, you’ll leave with actionable tips to streamline your day and deliver a five-star experience.

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Data is Powerful–Unlocking Insights: Deep Data & Reporting in Streamline

Discover how to tap into the full power of Streamline’s deep reporting and analytics. From accounting and reservations to business intelligence and operational KPIs, this fast-paced session will show you how to find and use the data that drives smarter decisions. We’ll highlight practical examples, tips for maximizing efficiency, and explore custom reporting and automation tools. If you want to unlock insights and take control of your data, this is your session. Don’t miss it—your reports (and your bottom line) will thank you!

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Flight Club: The First Rule is… Use These Features!

Discover some of the most underused but powerful features in your system. From customizations to communication tools and revenue boosters, this session will help you unlock hidden gems and streamline your workflow. Fast-paced, practical, and fun. Don’t miss this chance to make your system SOAR!

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Lifting Off: The New Document Experience

This session unveils a streamlined, intelligent document platform purpose-built for the unique needs of property managers, operations teams, and reservation staff. Learn how to create new documents from scratch with AI-powered features. Whether you’re scaling your portfolio or optimizing daily workflows, discover how the new document experience can help your business move faster, operate smarter, and deliver exceptional guest and owner experiences.

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Reach New Heights with Streamline Communication

Elevate your guest experience with streamlined communication! Learn how to enhance every step of the guest lifecycle using Streamline’s powerful tools and automation. Discover best practices that boost efficiency, drive satisfaction, and keep your team aligned.

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Soaring Through Progress and Possibility

In this session, we’ll highlight the key feature launches that took flight this year and give you a first look at what’s on the horizon. See how your feedback fuels innovation, how our upgrades elevate performance, and how we’re aligning as one team to chart the course for an even higher climb in the year ahead.

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STR WARS The Fight Against the Evil Empire

Join us for a dedicated session focused on the issues that matter most to property managers. We’ll discuss current industry challenges, share resources to help you navigate changing regulations, and highlight opportunities to make your voice heard. This is your chance to connect with peers, gain insights, and strengthen your role as an advocate for both your business and the vacation rental community.

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StreamSign Fast. Soar Higher. Earn More.

Discover how StreamSign Pro can do the heavy lifting for you. Free up your time, reduce errors, and create a smoother experience for both you and your guests, so you can focus on what really matters: growing your business and maximizing your revenue.

System

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Elevate Guest Experiences with Happy Stays

Discover how the Happy Stays guest app elevates the guest experience from booking to check-out. We’ll walk through setup, customization, and strategies to boost guest engagement, plus highlight key features like digital check-in, local recommendations, document delivery, and upsells. Give your guests the tools they need for a five-star stay, right at their fingertips!

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Launch into Success: Onboarding with Momentum

In this session, we’ll share a clear, step-by-step look at our software implementation process so you know exactly what to expect—and how to launch with confidence. Our onboarding project management team will highlight best practices, realistic timelines, and tips for a smooth, successful rollout.

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More Than Just Emails: Streamline’s Superstar CRM

Discover how Streamline’s CRM is so much more than just an email tool. From powerful automations to lead management and homeowner acquisition, this session will show you how to unlock some of the most impactful (and often underused!) features in your CRM system. Fast-paced, practical, and packed with real-world examples — don’t miss your chance to soar with your communication and sales workflows!

Revenue Management

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RevMax: Gaining New Heights with RevMax Dynamic Pricing

Take your revenue strategy to new heights with dynamic pricing powered by RevMax. This session dives into how dynamic pricing works, why it matters, and how to harness it to maximize occupancy and revenue across your portfolio. You’ll learn how RevMax adapts to market demand in real time and how to fine-tune your strategy for different property types or seasons. Whether you’re ready to leave flat-rate pricing behind or want to elevate your current strategy, this session will equip you to soar with confidence and control.

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RevMax: How Revenue Managers Help your Numbers SOAR

What exactly does a Revenue Manager do—and how can they help your business take off? In this session, we’ll dive into how Revenue Managers turn complex market data into clear, strategic pricing decisions that maximize revenue while aligning with owner and property manager goals. You’ll learn what data they monitor—like occupancy trends, comp sets, pacing, and demand signals—and how they use that insight to fine-tune dynamic pricing, adjust strategies in real time, and keep your portfolio performing at its peak. If you want to understand the “why” behind the pricing and how expert support can drive smarter, more profitable decisions, this session is your runway.

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RevMax: Learning to Fly—RevMax for Beginners

Ready to take off with RevMax? This beginner-focused session will help you gain lift in your revenue strategy by introducing the core tools and insights behind the RevMax platform. Learn how to navigate the system, understand pricing recommendations, and set your properties up for success. Whether you’re new to revenue management or just starting with RevMax, this session will give you the confidence to soar toward stronger performance and smarter pricing.

Team & People Managment

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Building Relationships that Take Flight

Strong relationships are the runway for lasting success—whether with guests, owners, or teammates. In this interactive session, you’ll explore different communication styles and discover how to adjust your approach to better connect with others. Learn to recognize key traits in yourself and those around you, reduce friction, and build trust faster. By understanding how people communicate, you’ll gain the tools to elevate every interaction and create smoother, more collaborative relationships that help your business truly take flight.

SLU

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Daily Flight Plan: Essential Tasks for Reservations & Front Desk

A practical sampling of some of the essential functions reservation and front desk teams rely on every day.

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Ground Crew Essentials: Key Functions for Property Care Operations

A practical look at some essential functions housekeeping and maintenance teams rely on to keep every property guest-ready and in top-notch condition.

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Turbulence-Free Owner Relations: Essential Functions for Owner Services

Discover some of the functions and best practices that help avoid bumps and keep owner satisfaction soaring.

Partner Collaboration

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A Practical Blueprint to Reduce Accounting Headaches for STR Managers (presented by Topkey, Dragonfly Accounting)

Join Jon Sukhia (CEO, Topkey) and Nicole Levesque (Founder, VPMS and Dragonfly Accounting) for a 20-minute, hands-on discussion on the five biggest levers to simplify your accounting process. We’ll share real-world tactics to get reconciliations right the first time, eliminate manual data entry, improve expense categorization, automate vendor payments, and make owner reporting effortless. The session is interactive, with time for audience questions and shared best practices.

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Adapting to an Evolving Distribution Landscape (Vrbo, Booking.com, Vacation Finder)

Change is a given in the short-term rental industry—especially when it comes to distribution. In this dynamic panel, leaders from Booking.com, Vrbo, and VacationFinder will share how shifting competition has pushed each platform to innovate, evolve, and elevate their strategies to stay ahead.

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AI-Driven Growth for Modern STR Managers (BestyAI, Bookings Cloud, Summer)

Today’s top STR property managers are using AI to move from reactive decisions to predictive, data-driven growth. This session explores how AI is transforming investment choices, guest experiences, and overall performance across the short-term rental journey.

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Drive Direct Bookings with Data (presented by Direct Booking Tools)

Boosting direct bookings is more achievable than ever. This session explores how leveraging data-driven insights, and the right technology can drive revenue growth, improve conversion rates, lower costs, enhance homeowner retention, and attract new property owners. Learn practical strategies and tools that make measurable impacts on your business.

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From Service to Standout: How Operational Excellence Builds Unforgettable Hospitality Brands

Join Breezeway, Lynx, and experienced property managers for a dynamic session on elevating hospitality through operational precision and brand-driven guest experiences. From frictionless self-check-in to thoughtful post-stay engagement, discover how every operational detail can reinforce your brand and set you apart in a crowded market.

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Investigating Revenue Blind Spots

If revenue is flat or falling, the real culprits may be hidden in plain sight. In this forensics-themed session, you’ll investigate overlooked issues, uncover real case studies, and build your own revenue recovery playbook.

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Liftoff: Payment Technology That Helps your Business Soar to New Heights

Today’s property managers need more than just basic credit card processing. In this session, we’ll explore how modern payment tools, like—PayPal, automated bank reconciliations, guest verification, and integrated owner payouts—can reduce friction, save time, and elevate the guest and owner experience. See how Lynnbrook is helping managers streamline operations and scale with confidence.

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Shaping the Future Together (presented by Rental Guardian)

As global travel rebounds and reinvents itself, the travel insurance industry faces a unique opportunity to redefine its role in a rapidly changing landscape. This session will bring together thought leaders, innovators, and industry experts to explore how travel insurance can evolve to meet the demands of tomorrow’s travelers.

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Soar with Strategic Owner Acquisitions (presented by The Rentalz Company LLC)

Leveraging the power of data to grow your business. How to create your owner acquisition strategy and turning your strategy into an executable plan. Industry peer best practices for planning, data, tools and execution.

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Squeeze the Juice—Get 18% More Revenue from Existing Properties with AI (presented by Enso Connect)

Are you leaving money on the table with your current property portfolio? Learn how to boost revenue by up to 18%—without adding new properties—using AI-driven tools that automate upgrades, predict maintenance, and unlock passive income.

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The Perfect Pour: Mixing the Ideal Tech Stack Recipe

Top vacation rental managers are tech mixologists, blending the right tools to build scalable, profitable businesses. This fun, cocktail-themed session shares real-world tech stack “recipes” to help you streamline tools, reduce waste, and drive results.

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Top 5 Back-Office Best Practices to Help Vacation Rental Managers Scale (presented by Avalara and Thuro)

A countdown-style session that highlights the best practices STR property managers follow—and the most common mistakes to avoid—when scaling. Avalara and Thuro will addresses key pain points from their areas of expertise (e.g., accounting gaps, tax missteps, operational inefficiencies), offering fixes and preventive tactics.

Roundtables

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Homeowner Acquisition in 2025

Learn how to cut through the noise to find proven strategies and messaging that works for your market. Meet with peers to discuss mailers, pro formas, and other means to attract the ideal owner profile.

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M&A Roundtable

What is my business worth and how might I prepare for a strategic exit? Meet with your peers to interact and discuss a candid conversation centered around M&A in the vacation management space.

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OTA Roundtable

Join us for an interactive roundtable discussion, facilitated by a Streamline team member, where property managers can share best practices, exchange experiences, and ask questions about leveraging short-term vacation rental OTA platforms like Airbnb and Vrbo. This is your chance to connect with peers, gain practical insights, and discover new ways to maximize your OTA success.

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Property Care Best Practices

Meet with your peers to interact and discuss all things Property Care. Roundtables are client-driven discussions, so bring both your tips and your questions to share during this time.

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RevMax Roundtable: Adapting to Shifting Travel Patterns

Travel behaviors are evolving—seasonality, booking windows, and guest expectations are changing faster than ever. Hear directly from RevMax Revenue Managers on how users of our software are adjusting strategies to stay ahead. You’ll walk away with practical ideas, proven tactics, and a clearer picture of how to turn travel trend shifts into opportunities for your business.

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RevMax Roundtable: Dynamic Pricing Deep Dive

Join our expert Revenue Managers for an inside look at how to unlock the full potential of RevMax’s dynamic pricing tools. We’ll share tips, tricks, and real-world examples to help you fine-tune rates, respond to market demand, and maximize revenue with confidence. Bring your questions and leave with strategies you can put into action right away.

Client Networking / Panels

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AI:Autopilot for Property Managers

AI and automations are past the “futuristic” stage—they’re fueling operations today. Hear how Streamline users are implementing different AI-driven tools to assist with decision-making, streamline workflows, and elevate guest experiences.

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Clean Skies Ahead (Housekeeping Ops)

Explore the optimized cleaning workflows designed to enhance efficiency and ensure the highest standards of cleanliness. Learn about best practices, step-by-step procedures, and innovative tools to streamline your cleaning processes

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Cleared for Landing—Guest and Property Safety

From guest screening and ID verification to guest and property protection, safety and trust are not just policies, they are peace of mind. Panelists will discuss the tools, processes, and tech stack they use to safeguard their homes and guests. Learn more about how others are evolving and staying ahead of emerging risks in the industry.

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Elevating with OTAs

Hear from different property managers – large and small – as they discuss their experiences with different OTAs. From optimizing listings to leveraging new features, this panel will give you practical insight and fresh ideas to elevate your OTA game.

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From Booking to Departure

From first inquiry to soliciting guest feedback upon departure, delivering a positive guest experience takes the right tools and touchpoints. Hear how fellow property managers are elevating guest experiences through communication, automation, and personal touches.

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Revenue Management– Filling the Gaps

Join Streamline clients as they discuss how they navigate different revenue management tools and integrations. From intuition to automation, this facilitator-led session explores the different ways clients are adjusting to optimize occupancy and profits.