Are you a short-term rental (STR) property manager feeling overwhelmed by messy books, unclear statements, or the complexities of trust accounting and multiple booking platforms? You're not alone. We speak with dozens of property managers each month, and while each has a unique story, the questions they ask are surprisingly similar.

Here are the top 10 most frequently asked questions from STR managers considering Keystone Bookkeepers - and how we solve each one.

1. Can you help clean up and organize my messy books?

Yes! Whether you're coming from a generalist bookkeeper, wrestling with spreadsheets, or migrating from a botched QuickBooks setup (especially one connected to OwnerRez), we can help.

We’ll:

• Implement an industry-standard chart of accounts
• Ensure all historical transactions are properly categorized
• Post historical owner reports to a single portal for easy owner access

2. Will you prepare monthly owner statements and ensure trust accounting is compliant?

Absolutely. We create detailed, itemized owner statements via VR Platform. Every reservation is broken down and reconciled to ensure:

• Only collected funds are paid out
• Your trust account is always fully funded for future liabilities

3. I use multiple platforms (Airbnb, VRBO, Booking.com, Direct). Can you accommodate all channels?

Yes. By connecting your PMS to VR Platform, we pull in data from all major channels. We also integrate directly with:

• Airbnb
• Stripe
• Guesty Pay

We even reconcile the tricky transactions that don’t fully integrate with the PMS - Airbnb resolutions, VRBO fees, payment processing fees, and more.

4. My bookkeeper doesn’t understand STRs - how are you different?

STRs are all we do. Our team understands:

• Trust accounting nuances
• PMS integrations
• Owner statements
• Co-host vs. property manager vs. arbitrage models

We know your pain points - and even the ones you haven’t discovered yet.

5. Do you file vacation rental taxes (like occupancy or sales tax)?

Yes. We handle monthly, quarterly, and annual occupancy or lodging tax filings across the U.S. and Canada. We also compare collected taxes to actuals to ensure your guests are paying the right amount.

6. How do I get you my expenses like receipts and vendor payments?

You have options:

• Email receipts
• Snap photos via our mobile app
• Upload to our secure portal
• Grant access to platforms like Amazon Business

We review transactions weekly and use Uncat to clear up any questions before month-end, freeing us up to focus on owner statements once the first of the month hits.

7. Can you track performance by property or owner?

Yes. All financial reports - P&L, balance sheet, owner statements - can be filtered by property. This makes it easy to assess individual unit performance and scale intelligently.

8. How do you work with Airbnb’s co-host payout structure?

To put it simply - we don’t. Airbnb’s split payouts are tough to reconcile and lead to confusing owner statements, especially since other channels aren’t handled the same way.

Instead our co-host clients:

• Have funds flow 100% to the owner
• We invoice owners monthly
• Invoices are backed by detailed, zero-balance owner statements

This keeps your books clean and cash flow easy to manage.

9. Can you support my business as I scale or switch PMS platforms?

Yes. We support managers with 1 to 150+ properties and work with:

• Guesty Pro
• OwnerRez
• Hostaway
• Hospitable
• Hostfully

We've handled dozens of PMS migrations - yes, importing existing reservations from VRBO is always difficult.

10. What’s included in your monthly fee?

Our per-property monthly rate includes:

• VR Platform subscription
• Owner statements
• Bank reconciliations
• Monthly management financials
• One-business-day email support, plus optional call support

Add-ons include:

• Monthly owner payouts
• Weekly vendor payments
• Occupancy tax filing and remittance

Got a question we didn’t cover?

Schedule a free consultation and ask away. We’d love to help you bring order to your books and clarity to your cash flow.