Other times they are trying to pay down their past due balance, and they aren't allowed to pay more than the monthly rent unless I log in and manually set up a new invoice for them as a one-time payment which is a headache for everyone. 

Though maybe they need a new system to match invoices with payments. :-)

I requested an itemized invoice for the dues payment from the broker and staff on multiple occasions and did not receive one.

Excel is perfect for your first project.You don’t need fancy software yet, a clean sheet that tracks:• Budget vs actual• Invoices/receipts• Category (materials, labor, holding costs, etc.)• What’s capitalized vs expensed• What’s part of unamortized loan costsOnce you set it up, staying organized becomes way easier.2.

I’ve only got a dozen properties but even without any input from my PM I might deal with 1 invoice a year if the tenant gets behind.

That means more of your cash stays in your business, not the IRS’s pocket.For many buyers in this market the ability to offset income and reinvest tax savings is a major advantage — and it strengthens your underwriting.Since STRs have strong appeal (friends & family groups, weekend escapes, high-end amenities) the sooner you position it as a business, the better your financial outcome.Your Step-By-Step Playbook for Cost SegregationHere’s a practical checklist to make cost segregation work for you in an STR:Buy/underwrite with tax strategy in mind: When you evaluate a property, include cost segregation as part of your operating model (not just nightly rate and occupancy).Engage a cost segregation specialist: You’ll want a qualified provider who understands STRs (they’ll allocate assets into proper shorter lives, document everything).Structure operations for “business” treatment: Track participation (guest communication, property maintenance, marketing) to lean into non-passive income treatment.Conduct the study early: Ideally in the year you take service (purchase or major renovation) so you front‐load benefits.Keep detailed records: Invoices, improvement costs, design/furnishing upgrades, hours spent managing.

  $400 for cleaning (I'm in Canada) would be a deep cleaning and should mean everything is cleaned (ie oven, behind appliances that are easily moved-fridge, stove).For $3500, they need to provide you with an itemized invoice. 

You’ve got three levers; pick the one that funds the highest‑ROI work with the least risk. 0% cards are fine for bite‑size, invoiceable items if you can pay them off before the promo ends.

Keep the installation invoice, permit info if applicable, and the retest report in your disclosure packet so the next buyer sees “issue found, fixed, verified.”

I.e. instead of simply giving an invoice, it is better if they list all the issues and then what specific cleaning was done, using what detergents/ chemicals including the time spent.