You need real insurance that covers the house when guests are there, or when it's empty in between guests. 

Does he want to use the house?

It also is helpful to have a California LLC in case you ever sell that property and move into another state so that you do not need to form a new LLC altogether with new operating agreement, just re-register in the new state as a new foreign LLC.

The first thing I ask is why am I Buying the property.I always look at the exit strategy first, is it going to be a rental, a lease option sell, am I planning on living in it.

I would not consider a house that cheap to be near a B.  

It would be like if someone prepared to sell by painting to create fresh visual interest, but chose fuscia and lime green...those colors would certainly catch the eye but I'd never claim that they overdid the curb appeal by painting with too much visual interest.

Waivo has a different but similar product they sell directly for STR.

More effort should go into enforcing existing permitting laws and cracking down on unpermitted work rather than imposing costly regulations that push property owners into avoidance tactics.If the goal is to improve fire safety in Worcester’s aging multifamily housing stock, the best approach is to encourage full renovations that bring buildings up to modern safety standards—not to place additional financial burdens on responsible owners.

And for reference my sister is dealing with a run down house in Louisiana that has a value of about $95,000 and she shopped multiple policies with multiple insurance companies and the best rate she could get was $2500.

I'd second house hacking.