At least people have ratings on the OTA and I can see if other hosts have had issues.

You are going to have "seasoning" issues trying to take cash out.

Zoning should not be too much of an issues, but uses may alter parking requirements. 

There's no benefit to anyone if they can’t rent the rooms, so your interests are their interests, and they're looking out for you - they actually recommended I back out of the first house I put an offer on due to foundation issues that they weren’t comfortable with.

There needs to be a major destination hospital nearby or large teaching hospital.

Just wondering what the implications are of changing a single member LLC to a multiple member LLC as far as current depreciation, basis, carry forward losses and any other issues. 

If so, would this still cause issue with the S-Corp tax rules?

There's a ton of information available on these forums if you're ever unsure about anything, take a look around, chances are another person has encountered the same issues and share their experiences on here.

The Management Company is recommending at this point, because there is a dispute, to send some kind of bill showing that this work was done and if not, it would be best to issue a refund.

I-if it's "big expense", I get ahead of this issue by whipping out a receipt book (you can buy one at any store like Target, Wal-Mart, Staples, Office Depot, etc) and jot down the work that was performed, materials, hours, amount of people, other expenses, etc.