My goal here is to create a golden thread that a beginner can follow to get to a solid rental investment that puts cashflow in the pocket and with an added element of a little fixing up, the potential to complete cash out and do again with the same money every six months.

good question, following

I'll be reporting to flight training located in Pensacola, FL with the Navy following graduation. 

I think the majority (not all) of people who say they can't pay really can.I think about the following when given a situation like yours:  If you give them the free rent, then why not head down to the local shelters and find other disadvantaged people and offer them free rent as well? 

@Ritch Bonisa i have been mostly following the CMA prepared by my agent.

Like @Stanley Bronstein said, many communities have VERY strict rules about AirBnB's or STR.  

If you search long enough, you might find a title company that will insure title for you.If it were me, I would let the HOA foreclose and follow up right behind them with your own foreclosure.

He's interested in flipping up north and isn't sure if his contractor will follow. 

You certainly can follow someone without that person even knowing they are your mentor!

Not surprisingly, most endowments and pension funds follow a similar investment plan.