It was enough extra money to keep them interested and you set all the showings for the same date and time anyway so it's a few hours a week when there is a vacancy. 

I checked airbnb and vrbo and there are very limited options there for such long leases over the summer in Pensacola. 

But the agreement made it very clear I would not set up a PM because my brokerage has an existing PM arm.

With Property you know the limit of risk you are taking, but with Liability claims, you never know, so best to keep that with the carriers. 

If you’re looking to go more of the passive route, you may want to look into investing in syndications as an LP(Limited Partner).

Normal state rules would limit ADU to 50% of current dwelling.  

I have seen some states require that you have a licenses, so don't require it, some put a limit on how big a job you can accept, or how you advertise.

We are limited to your 2nd hand knowledge. 

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I would avoid buying your first property in all cash since they would limit how quickly you can scale your portfolio.