Short Term Rental Applicant wants to book the "whole Summer"

[John C.]

We purchased our first Short Term Rental, a penthouse in Wildwood. Posted it on Airbnb, VRBO and Facebook Market Place. It's $2700-$3400 a week which I'm being told by other owners is about normal. Ours seems to be one of the nicer ones.

I had someone contact me on FB asking to rent the whole Summer at about a 10 percent discount paid half now and half at check in via cashiers checks.

I informed him that we already have a few weeks booked and that he could book around them. Coincidently this makes three bookings the longest of which is 29 days.

He has agreed to pay $25k total and sign three seperate contracts with $12.5K cashier's check being paid now (about a month before first stay) and another $12.5K at the check ln also cashier's check for first stay. So the first 12.5k will clear before first stay begins and second 12.5k before second stay.

I am a little uncomfortable because this seems too easy... He asked some questions but not as many as I would before giving up 12.5k to someone I don't know.

His FB profile looks legitimate.

Any thoughts? These are the questions I have:

Is this a typical request?

If each contract is for 29 days is there a risk of tenants rights? Squatters?

What are the greater risks with this arrangement than one week?

If I choose to go ahead how can I protect myself?

Would you do this?