We eventually refunded the loan with our preferred bank but not before losing a boatload of cash to the ‘hump’ in the road.

You don't mention it, but if you are planning on moving in the next few years, I'd rent rather than buy unless you plan to eventually turn the home into a rental.

If you decide not to invest where you live, it's really important to know the different neighborhoods and price points in the market where you'll eventually buy. 

The deal has to work even when the market turns cold because all markets will eventually turn cold.

I will be eventually making the move to Florida.

Also, how did the transition work when you eventually left the house and started renting out all the bedrooms?

If you don't have the time or resources to check on your vacant property at least weekly you're going to find yourself a victim of these things eventually.

Currently renting out the secondary bedroom and using that income to make improvements/renovations to the place, with the eventual intention of turning it into a rental property when I leave the military next January.

It also ensures we have rent growth which makes any so-so investment a great one eventually.

To your last question: not currently, but "eventually".