Ours was an occasional rain issue in one corner and also a bit of an uneven floor. 

Is he required to issue me a 1099 form for rental income for 2023 taxes?

Can we deduct the office as a business expense since its sole purpose is working, or would splitting the use between a W2 job and rentals create an issue? 

The investment game is all just math—if you do the math well (which includes accounting for the unexpected by low-balling your estimates) then your investment decisions don't have to be stressful emotional ones, they're just decisions that are either smart or not smart after you break them down on a calculator.Which extends to the last point that I've come to believe completely—your rental portfolio is a business.

I think this makes everything cleaner for taxes, documenting historic rental payments, and legal issues that may arise due to the barter, etc.  

With some of the CapEx issues/concerns that came up during the inspection/prep work for construction, we delayed some of the work when we should have just addressed them all ahead of time.

The HoA can issue a citation for the yard being full of weeds and that they would be responsible for paying the fines. 

Obviously, this is a speculative question and nobody has a crystal ball on this issue, however, I think close consideration of the fundamentals are important in making a decision about this.

I meant you need to take care of that issue.

Hi everyone, I want to issue 1099 to my contractor to be on the safe side. 1. what 1099 should I issue to them?