@Anirudh Goel Do you not qualify for the loan if this is not resolved?  

When dealing with 5+ I would make the argument it may even be easier to qualify for a loan. 

Their timeline (NACA) is prob 6-12 months which is too slow for many people but sounds like a potentially good fit for you.If you are paying rent on top of your student loan debt, employed, and have ok credit, you should be able to qualify for an owner occupied duplex with NACA.

If you decide you want to flip Properties from your IRA, you must know that such a process is a competing business and as such, UBIT (a complex form of taxation for qualified retirement accounts) will kick in.

The house is now boarded up and vacant, with a sign on the door that the city plans to demolish it, if it is not brought up to code. 

No one on this board can provide a true answer.

I’ve had the idea of house hacking my first investment, Just to get a feel  and some skin in the game.  

In preparation for that moment I would recommend evaluating/analyzing the investment to better understand what is required.I believe that Opportunity Funds will present a rather large incentive to those wishing to "cash out" on their investments by selling their assets and exchanging their proceeds into a qualified opportunity fund.

It sounds from your description that it is.However, because you also do personal activities in the room (play games on your desktop), it doesn't sound like this would pass the "exclusive use" rule.Playing the games on your laptop in a different room would likely qualify the room as "exclusive use" as a home office.Also note that in the future if you take this deduction, there is a simplified method you can use to reduce the records you have to keep - just multiply the square footage of the office by $5 (if it is under 300 total square feet).

They have more skin in the game then you do.Make sure you get clear title.