What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

A couple ideas below:- Have tenants pay utilities if they don't already- Refinance into lower rate- Increase rents (or convert to mid term/short term rental or rent by the room)- Call the county tax assessor's office to ensure there was no mistake in the tax increase- Call your insurance broker to get you other quotes- Sell the property and 1031 into a better market that does not have those issues- Self manage if you currently have a property managerHope these help!

Since the market pre-May 2022 just is not comparable anymore I am interested in anyone who has done this in CFL from around May 2022 onward successfully and how it went.The goal would be to aquire a STR that would cash flow itself, or at worst break even and also use that to maximize deductions to lower W2 federal income tax.

Non-paying tenants and going down the eviction process are the worst!

I know this was my mistake for not getting them before sending the money he requested (he'd done a couple rehabs for me before and it wasn't an issue). 

That was a huge mistake…to say the least.

What kind of documents would I need to cover both of our ends in any worst case scenario and where could I find some examples?

I recommend you talk to an attorney to avoid making a legal mistake that permits them to stay longer.

@Carmen Assang you are your own worst enemy!

These days it can be hard to tell but sometimes it's just so painfully obvious, and that's not the kind of content we want to reward because as you mentioned AI will sometimes at best embellish and worst fabricate or hallucinate fake information.