I check county records, tax records, current appraisal from the local municipality, and check for comps in the local are with respect to the properties condition. 

It might not make a difference to you, but your tax pro and bookkeeper will hate it. 

The income on this one is a little confusing, but from what I can gather, WorldQuest has a yearly average nightly rate of about $220 and they claim about 85% occupancy.

My only income is 1099s, which I write off a majority of it to lower my taxes.

I bought these properties cheap, had them fixed up and not have they appreciated a lot that also generate a nice tax free cash flow that goes back into my IRA to be redeployed into more properties.This is a huge tax free money maker. 

I then contacted them and asked for a refund, which they claimed to not be able to do because of their policy, which covers them and allows them to do whatever they want after the initial 30 days is over. 

No, it was a single 30-day stay.Proof is not required when you file your taxes.

It sounds like you are looking for an employee as defined by most taxing bodies.

You won't have to file a state tax return with Tennessee as they don't tax rental income.You likely want to work with a CPA who understands the different state tax laws.Good luck in your search

Based on IL law tenant cannot ask for rent refund.Question, shouldn't the platform work with the tenant with to void the wrong claim since the platform has lease and all the transaction information that's the payment for February rent?