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 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. 

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). 

Not that it cant or wont, but unlikely.If OP applies for homestead on a new property, then I personally would not lie during the application about receiving the exemption on the existing property.

Many banks limit personal loan amounts.

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.

And always check social media for red flags and I agree with Vince, always meet a person.  

Yes I have known it to work because the owner is not a push over, enforces policy and can make it run good......however, do you have the right personality to do this, AND if you move out can you continue to have the house run smoothly with no one in charge.  

@Brody Trott you'll want to run the numbers on as many duplexes in your chosen market as possible.