So I'll say this:Get a lawyer (lol) if you care a lot about this door jamb.But...My gut says, if you don't like the door jamb repair on their end, keep the security deposit money required to repair it to it's original condition.

. - Accounting, not mentioned, but make sure you can confidently run the trust accounting and security deposit which is compliant with state code. - VAs, I don't think this is necessary for 30 doors, but depends on how much availability you have and how time consuming these properties will be.

We also have our Courtney Clause .. which states we can terminate the contract give them their deposit back and 500.00 at our sole discretion if we feel we are not getting along and the buyer is just too difficult to work with .. we have had to bring that to the attention of some buyers and their agents to bring them back in line.. 

The problem is you don't know if someone just made a large deposit to make them look good and then the money is gone after they move in.

If booking direct and he has no reviews I would have him sign a simple lease, do a BG check, and have a reasonable deposit.

I would avoid this if its your first acquisition  but you also appear to have enough cash to complete the purchase without financing so you wouldn't necessarily be at risk of losing your deposit, only incur additional transactional costs.

If you are showing monthly deposits of the same amount each month that are in the amount of a rent, you would need to show where that money was coming from and going to, as in which address it applied to.

I accepted a prospective tenant's lease and deposit after doing due diligence.

In most situations the tenant is 100% responsible for the initial security deposit payment, and any recurring utility charges. 

There are several types of fees on Airbnb specifically: -Airbnb service fee, cleaning fee, extra guest fee, pet fee, security deposit, VAT (if applicable), and local taxes.