You have not added to much difficulty in terms of tax preparation, but in terms of tax record keeping you definitely have.I am not a tax professional, but having been a landlord who has tried(and failed) in my own tax situation, I would love to help point you in the right direction.Being your first year, it is all but a certainty that you have taken a loss.

I've tried Air BNB support to understand what the prior quality issues are to prove we've resolved them (but for privacy they can't tell me).

This gets people burned too many times by getting comps from a wholesaler, believing the comps, and then trying to sell it at that outprice that the wholesaler/bad agent gave is a huge miscalculation.

Has anyone tried it and had success?

Now, the TLDR version of my previous post:"Exit Strategy" is a big word for what I am trying to do: acquiring a modest home in rural Arizona at a cost of:1) About $15,000 in cash.2) Tying up another $200,000 four nearly four years at very low interest rate return.

I’m not trying to cheap out but I can do a lot with that.

If your really needed it one could also consider hard money though that will come with higher rates and getting someone to give you 300k first time might be harder than just getting loan then you could refinance it later.Since your a high net worth person I would also try talking to local/regional and even big bank lenders.

Currently we are finalizing paperwork and figuring out what insurance we need and just trying to figure everything out all at once.

This is a good tenant of 5+ years, and I don’t want to cause unnecessary friction (I’m just trying to set up automatic systems for myself).

Try to understand the relationship and what's going go.