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.

First, your tennant is valuable, even if they are getting their deposit in at the last minute. 

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.

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. 

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.

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

Our average online rating is 3.5/5, which is 60% higher than the 2.2 star average of traditional property managers.Sometimes we need to make a tough decision in favor of one side of the landlord-renter transaction and at a negative impact to the other side (i.e. deducting security deposits).

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

I lived in Superior for a while and commuted downtown every day (get satellite radio ha).I'm a realtor, so fortunately I have instant access to what is hitting the market and it's still very hard to find something before 50 other people have found it as soon as it hits the MLS.

I would charge it now so that it doesn't need to come off the deposit at the end leaving you with more deposit for any other damages.