Any legal issues I should be aware of in this situation? 

The only way for you to understand the situation and evaluate your options is to ask a lot of questions.  

Location. 25 minutes to beach, 40 minutes to Florence, 15 minutes to Pisa, 60 miles to snow skiing.  10 minutes to Home Depot style store, etc.  

Just know others are in the same situation--I'm stressing about one of mine too!! 

I don't know your living situation but if your paying x,xxx for rent or a mortgage and instead by living in one side and renting out the other you will be paying y,yyy instead and y is less then x that's great, especially if you can rent out your primary residence and make income there too. 

I paid off 19 units last year - 17 apts, a store and a house.

I am in the same situation.  

Currently situated in San Diego and can only afford rent for now because house prices in SoCal are bonkers.

Yes been thinking a while about what to do after selling property:1. just pay the tax and paying off debt as you said2. 1031 DST with lower return "slightly higher risk" investment3. or QoZ funds where it's the riskiest investment/10 year money out with the investment into developmental phase/cycle location (hence lot of gambling) at the worst of time.It's win-win-win situation for uncle Sam :)

Regarding the condo/townhome situation in Fort Myers vs Bonita Springs, I would say the more important things to focus on would be the association fees charged, what is included in those, and the rental restrictions of the association.