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The 1099 Filing Playbook for Property Managers
A Repeatable 1099 Process for Property Managers.
Wednesday, January 7, 2025 at 10 am PST
Zoom
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One wrong homeowner 1099 can turn tax season into an expensive and stressful mess, and nothing damages trust with owners faster than incorrect reporting.
But it doesn’t have to be that way.
This session is designed to give property managers and accounting teams a clear, repeatable system for preparing, validating, and filing homeowner 1099s - so homeowners feel confident, supported, and taken care of.
Ben Coons, CEO of Keystone Bookkeepers, an accounting firm supporting 150+ STR management companies, will teach you how to streamline your entire 1099 process so you can file accurately, avoid errors, and keep your homeowners happy.
If you are in charge of filing 1099s on behalf of your homeowners or vendors, this webinar helps you protect relationships, avoid sticky tax-season conversations, and give homeowners the peace of mind they expect from a professional manager.
By the end of this session, you’ll know:
- How to prep for year-end filings using clean vendor naming conventions across Topkey, QuickBooks, and payment systems
- How to confidently read and verify W9s so you don’t request corrections mid-season
- How to use a 1099 Decision Tree to determine exactly which homeowners or vendors require filing
- How to use your PMS as your source of truth, ensuring numbers match across tools before they go to an owner
- How to pull and organize 1099 data based on your PMS with workflows shared by Keystone
- How to file 1099s accurately the first time, maintaining owner trust and reducing tax-season escalations
Sign up now to join live and ask questions, or sign up to get the recording.
Speakers
Keystone Bookkeepers partners with growth-minded short-term rental operators and property managers to deliver accurate financials, tax-ready books, and strategic insight that drives growth. I founded Keystone to help STR entrepreneurs move beyond messy books and reactive accounting.
Too many operators are flying blind - managing multiple properties, juggling expenses, and trying to make sense of their numbers only at tax time. We help you get proactive with your finances so you can make smarter decisions year-round as well as provide accurate owner statements on time to keep your homeowners happy.
Our team specializes in the short-term rental industry, so we understand your business model, your tech stack, and your pain points - from owner statements to channel management to cleaning fees. We deliver clean, timely books, streamlined reporting, and financial clarity that empowers you to grow profitably. Whether you’re managing a handful of listings or scaling into multiple markets, we’ll help you understand your margins, forecast cash flow, and make data-driven moves with confidence.
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Darren Carter is the Head of Strategic Partnerships at Topkey, the leading platform for helping property managers automate their finances. Before joining Topkey, he spent over 13 years at various technology companies, specializing in fintech and startups, including founding and selling his own company in 2020. He lives in Boulder, CO, with his wife, puppy, and newborn baby daughter.
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