This structure will let you capture the capital gains on the land thus far without it triggering capital gains taxes (assuming you don't trigger any of the limitations on the sale of your personal residence, or the gains are more than the exclusion). 

I just want to know all the issues/risks and see if they are valid before I pull the trigger on more purchases.

If everything makes sense at this point, pull the trigger!

I would do a lot more due diligence before I pulled the trigger, though.

You are stuck at a market price offer and not willing to pull the trigger on that. 

My resources include:- The VA Home Loan- By the time I move, roughly around $30K-$50K of my own working capital- A real estate partner and mentor based out of Chicago- My brother, a real estate broker who I can go to for access to MLS- Currently trying to build relationships with lendersI got out of the Marine Corps at the beginning of 2015 and have spent since then learning everything I can about real estate investment before trying to pull the trigger on anything.

Is there a trigger or sign that one should be keeping an eye out for? 

I'm looking at Twin Falls specifically, but need to do much more before pulling a trigger on a home there.

As you can see - subject to interpretation.A commonly accepted trigger is when you start advertising the property - either online, by listing with an agent or by placing an outside sign.

It doesn't help that the National Floodplain maps are outdated and universally acknowledged to be "politically influenced" (as certain neighborhoods in Houston demonstrated).Maybe it's a bit short-sighted but with plenty of solid places to invest (major cities with booming job markets), it makes pulling the trigger on Florida an unenthusiastic choice.