I’m moved to have secured my first deal!

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

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.

You won't be an expert in all of the trades. 

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.

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.