- And more...Let's move past all of the above and focus on understanding and monitoring maintenance charges PMC's bill to their clients.There are two basic components of every maintenance bill, labor & materials.

How about a sales contract with contingencies but with a limit where the buyer can only terminate the contract if their find material defects exceeding a certain dollar amount.

The house's exterior is constructed of brick material with a flat tile roof.

Line Item Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $500 Business Hour Service Calls $80/hour + Materials Cost + Tax After Hour Service Calls $110/hour + Materials Cost + Tax HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Vendor Cost + 10% Oversight Fee

Type Line Item Fee Fixed Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $600 Variable Fees Business Hour Service Calls $90/hour + Materials Cost + Tax After Hour Service Calls $120/hour + Materials Cost + Tax 3rd Party Coordination HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Negotiated Vendor Cost + 10% Oversight Fee  

Line Item Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $500 Business Hour Service Calls $80/hour + Materials Cost + Tax After Hour Service Calls $110/hour + Materials Cost + Tax HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Vendor Cost + 10% Oversight Fee

@Jonathan B.Assuming you pass the "material participation" test for 2023 and did not use the property yourself (or used very little), you should be able to treat it as an STR for 2023, including bonus depreciation.  

A good baseline is to calculate material costs (e.g., $300 for paint and supplies) and add a fair hourly rate for labor.

What is the best way that you have found to tell them that you need labor & materials separate, so at tax time you can send them a 1099 for labor?

Materially participate in the property - this is the big one.