for me  a handful since early 80s  now in those days I was ONLY buying land that had owner contracts on them. 

It looks like according to the county site (sbcounty.gov) they require all renter payment go to the active owner. 

So my fear is, I would get someone all geared up to purchase a home and then the owner on the Deed would give me a hard time.

If you were to buy direct from the owner you will get great deals!

I've built relationships with property managers who have distressed properties in their portfolios that can communicate directly to owners. 

Put aside if the owner of the home is a family member. 

Property owners in these areas can only advertise for monthly rentals and are not permitted to offer daily or weekly rentalsandIn March (2024): Florida lawmakers passed legislation granting the state more authority over short-term vacation rentals, potentially impacting local regulations. 

Honestly, I've given up on finding cashflow anywhere close to the city due to rates and prices, BUT some other opportunities you may want to consider are:Live in flip - mentioned earlier in this thread, always a solid option in any market.Condo conversions - good money to be made from this and since they're a little trickier than a traditional flip there tends to be more inventory available that would allow for a profit.ADUs - come February 2nd, ADUs are allowed BY RIGHT on any SF property in the state, owner occupied or not.

My proposal is to do the following:1) Create an LLC in which my partner and I are both owners/operators2) Have the title of the property put into the name of the LLC via quitclaim deed3) Have the Operating Agreement of the LLC outline ownership based on shares ownership model.

Know this:  the #1 reason why landlords fail according to the American Apartment Owners' Association is failure to manage to the lease.