We require first and last month's rent and security deposit prior to move in.

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).

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

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.

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.

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

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.

Instead of increasing rent, I would look at having the security deposit increased to protect against wear and tear.

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.

My biggest hurdle has been securing financing to work on multiple projects simultaneously.