Make a simple spreadsheet or written list with the features of each and see which ones appeal to you most.

Our local market in Columbus has been pretty incredible with price points lower than markets like Austin or Nashville, with a better economic outlook than similar large cities of over 900k people. 

Will we approach other investors to do the deal with us or do it on our own? 

I've temporarily moved to a referral network only, and am very happy to answer questions and connect investors with real estate agents, property managers, and other service providers in NW Florida. 

They are legit.I have never done business with them, but I have acquaintances who have used them.

Whenever I am having an issue with financing, I normally reach out to local institutions.

This will be a great addition to your toolbox, especially with your experience.

Also, because your unit will probably be booked with a guest most of the time. 

I'd like to add that for anyone else wanting an to convert their primary property one day build good relationships with your neighbors in the mean time.

If you are buying a high cost property with litle to no cash flow, you likely don't have to worry about paying tax on rental income since your depreication will wipe out any cash flow from being taxed.