I would like to connect with a contractor that I could likely use and have on my team for future endeavors. 

Of course this puts all your eggs in the same basket and a Financial Planner might have a fit if you suggested the strategy to them.Of course there really is no reason why your non-profit can't purchase the building, especially if there are multiple tenants, it increases the amount that you are able to pass along through you endeavors.

I am in a situation right now with USAA where they dropped my umbrella coverage because they consider my rentals as a commercial endeavor.  

, I stumbled on the idea of going the duplex route with the plan of back tracking to an SFR later (IF) we had to.Without becoming a blowhard, fast forward a period of hard knocks (a very necessary process in any worthwhile endeavor), I’ll say this.

I have wanted to have my brother in law as my partner in this endeavor, as he is well rounded and would be a strong GC in terms of lining up contractors.

I wish you much success in your future R.E. endeavors.

Bigger the mess, bigger the transformation.

I bought my primary residence in DC but found that it was a little too inflated to be a good setting for the start of my real estate investing endeavors.

The first deal is transformational.  

Best of luck on your endeavors!