Ive analyzed a few deals in the past but could never pull the trigger and this is the end of that, just super daunting going at it completely alone :)Looking forward to hearing from y'aaaaall.

I guess the first question is whether the condo conversion would trigger some sort of due on sale clause with that original mortgage. 

You need to make sure condo rules do not state only a certain percentage can rent out the units they own.You might want to wait for a property that has less (hair) on it as we say in the business for your first one.

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?