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).

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.

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.

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

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

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.

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.

I can have separate bank accounts, debit cards, security deposit accounts etc. and now with new features like automatic recurring transfers things are even easier and time efficient 

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

Things to consider: daily internal operations, external branding and operations, lending, in addition to inside out *legal protection and outside in** legal protection, privacy/anonymity/identity protection and security...Prevention measures at different levels, preventing the attack from being initiated vs preventing the attack (lawsuit) being successful vs reducing the damage of a successful attack.... there are many elements and I see people pick one and argue about it without looking at the whole