You might make the most popular push a single family rentals and they are just too risky. 

I think your plan is great, as long as you follow through. 

At the meetings you go to try to meet other attendees and follow the general advice on this site by seeing how you can add value for them. 

Heck, I hired one of my staff while she was still on a walker following major surgery, and she's only 28.

But you do have to follow the law and the extra steps involved in evicting military tenants.  

At some point did you feel like the deal want going to go through and what was your motivation to keep pushing when you were faced with so many road blocks like the roof needing to be updated?

That is going to push the 'danger zone' of hurricane damage further inland and leave beachfront even more vulnerable.  

Subject property + other colateral to secure loan... rehab with credit cards... sell or refi to payoff cardsHard Mondy rehab loan... expensive loan against purchase and rehab... followed by a refi.These are some ideas...

Follow Dave Ramsey baby steps (maybe this should be number one).

In my gut I knew not to lease to him, but I didn't follow it.2.