Quote from @Matthew Crivelli: Personally, I'm not a fan of Air B & B.

Personally, I would hang on to the cash.  

Personally, my primary residence has appreciated around 6% in market value and I live in Levittown. 

The challenge was balancing the relationship between landlord/tenant and a personal/friendly relationship.

The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance. 

Many banks limit personal loan amounts.

If you feel the need for in-person mentorship, reach out to prominent local investors and try and strike a deal to learn from them.

The flippers we personally work with in California have not run into this issue (as far as I'm aware).

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

I have known and worked with Matt for years.I have attended his training and hired him as a consultant.He is hands down the best at what he does.I have personally raised over $50 million for my hard money lending company.I am grateful for a lot of people who helping me with this success and Matt is at or near the top of that list.