House Hacking vs. Single Family & Turnkeys

[Art Maydan]

So here's my situation: I'm 23 and my wife's 21. I hate my job and my chosen career path with the passion of a thousand suns and have decided real estate is how I'm getting out of it. My wife's about to graduate and has accepted a job as a teacher, which is something she does want to do. I'm pre-approved to buy a house with FHA, but my approval limit is very low because of how little I make ($210K for a 2-unit up to $320K for a 4-unit).

We need to have a Chicago address by August in order for my wife to be a teacher here. We’re having a hard time finding multi-units to house hack that are in our price range and are also in decent areas. Here are the options I see:

-Buy a single family home here in my name, live there for a year, then buy a nicer multi-unit with FHA in my wife's name in a year, house hack it, and rent the single family. Pivot from there.

-Keep looking for a multi-family that fits our criteria. This is riskier since it’s April and we need to be in the house by August.

-Buy a single family home and use turnkeys to invest in real estate. I won’t be able to afford a conventional down payment on anything decent in Chicago for a while. But I could probably swing a new single family in Ohio a couple times a year.

I’m only interested in buy-and-hold (for now) and I’m not interested in investing or living in the ghetto or dealing with Section 8.

In Summary:

Short Term Goal: Own a home in Chicago

Medium Term Goal: Quit my job

Long Term Goal: Become financially independent using cash-flowing real estate

Am I missing anything? Which route would you take in my shoes?