Quote from @Laurens Van swol: We are exploring the possibility of purchasing an investment property in Florida.

We actually CAN'T explain what we are seeing if we are operating on the "purely rational actor" hypothesis (as you implicitly observe), we MUST include highly irrational and emotional individuals to explain what we are seeing.- Investor uncertainty.

We are now married and I expect we'll file our 2024 taxes jointly.

We are three hours away from the properties .

We are developing as RV /campground - tiny homes on wheels - where is your property?

We are paying cash to him every week or so when he sends bill. 

We are asking the current tenants to leave as the property is not in optimal condition we like to have our rentals and we would like to fix it up to increase value and rents.

The other thing I have done especially if we are approaching winter months is just tell the insurance company that we will have them done in spring.

Ensure you have an itemized invoice from the cleaner, which can help justify the deduction.Reasonable Deductions: Long-term tenants often leave normal wear and tear, so I recommend being lenient on minor issues.

Between the two of us, we are pretty involved in real estate.