Yes, I'm aware of the $2,500 non AFS limit and each invoice is under that.

Give the tenant written notice and an opportunity to cure if you want to be conservative.For LVP:Light surface scratching is wear.Gouges, deep scratches, swelling from moisture, or plank damage is damage.For walls:Minor nail holes and light scuffs are wear.Large holes, heavy marking, or patchwork is damage.Make deductions based on actual invoices, not estimates.

I did not question maintenance items or request invoices previously because I operated in good faith and assumed transparency.

Not the repairs themselves, but the coordination:-Getting vendor availability-Making sure the tenant lets them in- Getting the invoice/receipt- Documenting for taxes and complianceI've tried spreadsheets, Buildium (overkill for my size), and just texting.

If your contractor lumped everything into one $60K invoice, it's worth asking them to break it out.

They mention pitfalls associated with using Zelle and such, and advocate for using a platform that generates an invoice.

Booking.com processes the payment, so they should be able to provide a proper invoice.

You really shouldn't have to, "manage the manger"😮In our opinion, you just want to understand what's going on with your property(s) and look for honest mistakes they may make.We had one where we accidently entered an extra "0" on an invoice.

Typically they track:DateProperty/unitVendorDescription of workCategory (repair vs improvement)AmountLink to invoice/receiptKeeping digital copies of invoices in a folder system that matches your spreadsheet (by property and year) saves a lot of scrambling later.Some use property management software so maintenance requests, invoices, and payments all live in one place, which makes year-end reporting easier.

The correct treatment often comes from:- the engagement letter / invoice detail,- the underlying contract,- who the beneficiary was (business vs owner),- timing, intent, and materiality,- and sometimes just a quick conversation with the client.And that’s why good bookkeeping/accounting isn’t “data entry.”