@Zach Scherschel part of what I was getting to.Insurance in Florida and California right now is a puzzle as many Underwriting companies pulled out. 

Hello Elana, Finding the right property management company is the most important piece of the puzzle.

But we'll at least take our first exploratory trip to see what's what down there. 

Cashflow is just 1 piece of a very large puzzle to determine which market to invest in. 

HELOC is the greatest tool for financing your real estate deals, I was referred to Mr Salman in 2016 and with my existing HELOC of $320,000, I was funded $517,000 for Rehab in Brielle at 3.99% without cashing out from my HELOC.feel free to contact him for your financial needs.Mr salman is a HELOC professional and will help solve all your HELOC puzzle/problems 

I include crossword puzzles and board games with my beach house STR/MTR.

To be candid, I have never done it myself and might be missing a major piece of the puzzle but I don't think so.

In my experience a good housekeeper who can manage a schedule and their own team is the most important piece of the puzzle to have a consistent listing. 

The partners are often the right people to solve only a fraction of the puzzle. 

Chiming in with my two cents on what process & cost would look like for permitting a previously unpermitted ADU in San Diego.Similar to bringing an illegal addition into compliance, it would require drawing a plan for the existing ADU (typically $2-3K), sending it to plan check at the city (planning, building, and fire), potentially conducting an exploratory phase where walls are opened up for inspection with the city (typically no more than $1-2K for opening walls and repairing them), addressing anything in the structure that is not within compliance (cost will of course depend on what’s going on with your structure), and paying for any permits (typically $1K).