Option Fee, Security Deposit, etc) can you do it with no money out of pocket?

Like the others said, I don't see how VRBO would even know you had a direct booking, or what would make them think they're privy to commission on a booking they didn't secure.

Cons are the liquidity event that your parents will have to do to purchase the home (I assume the funds are in some sort of investment today so there's likely some tax ramifications on cashing those securities).

You would choose the tenant so you would have a decent amount of security on who is living there.

There’s no specific IRS rule against refinancing a cash purchase and deducting the interest, as long as the property is used for investment purposes and the loan is secured by it.

With really bad credit I do require (in addition to first month and security deposit) 1/2 to a full last month's rent and/or a good honestrenter.com score.

Your conservative approach to estimating income provides a solid buffer, and the strategic location adds a layer of security.

The cleaner can just let you know when it's time to restock supplies. 

The fed did lower rates more or less directly in 2008 when they started buying agency mortgage backed securities which sets mortgage rates directly.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.