I am looking to network with professionals focusing in the cities of Indianapolis and Terre Haute or just hear sound advice from an experienced professional.  

It sounds like it is rent ($2500) - expenses ($2208) = monthly cashflow of $292 which is still decent (depending on how much you put down).A few things that jump out to me though are: $1200 HOA fees!

For what it's worth, it will not be our primary residence until years down the road depending on how things go (when we "retire"), but it sounds like, regardless, we should steer clear of both options (LLC and fancy self-directed IRAS) unless we want the LLC for pure liability peace-of-mind if we did somehow rent out the land or a structure on it (if it wasn't our primary residence).Thanks again for taking the time to reply, still figuring it all out and this really helps.

Fannie and Freddie have these deed restrictions and they're rather annoying but there's really nothing you can do but wait. 

All goes according to plan my fiancé will have a real estate license by the end of October and I will start my next full time job on Oct, 8th.I am concerned about my eligibility to obtain a loan and would like to know if anybody has advice on how they would go about tweaking numbers by paying down debt and lowering the down payment to lower the Debt to income ratio to get approved or if they think I sound like I’m in a sound position.

All of this sounds logical, and I will take your advice and talk to an attorney who specializes in this area.

You mentioned waiting to save up all the cask to do it all yourself and that sounds doable to you but the seller may not be willing to wait for you.

We had paid cash for a retirement property in 2011 (very cheap then) and we sold our big paid for house overlooking Puget Sound in 2013. 

I’m just guessing that if you’re in a $90k price range or less then you should absolutely go for a 3rd property, just get the other 2 rented and get yourself comfortable but sounds to me like a marvelous opportunity to rapidly scale your investments!!!

It sounds like it is above the price point you are targeting, but it may give you some ideas based on the house-hacking method we used as an alternative to buying a multi-family!