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.

We also had to replace the fireplace tile and grout because we couldn't get the urine stains off. 

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.

I moved in March 2017 and have updated all the flooring, all the windows, painted, replaced trim, adding gutters, rehabbed the guest bathroom and there’s more to come over time. 

My goal is to supplement my income and ultimately to replace it.

You probably shouldn't be ripping off shingles to replace roof decking as your first DIY job. 

If your priorities are to invest for income to replace a 9 to 5 personal home ownership should be way down your list of priorities.

Check when the roof was replaced and the age of the mechanicals too.Good Luck!