Make sure to reach out to one with real estate experience as location is not longer an issue.

I would like to be able to own a multi family unit (4units or less) where I can live in one of the units.

I really think this strategy can work for anyone and can really help launch you off into the direction you want to go with real estate wether that be cash out refinance, HELOC, another FHA, conventional, BRRRR, large multi family , single family, arbitrage , STR, MTR, LTR etc.. 

When it comes time to negotiate, the buyer will have his/her opinion on the matter so I’ll be somewhat dependent there, but it’s good to know the tax “mechanics” won’t be an issue and have a few reasonable options.Quote from @Michael Plaks: @Matthew HeffernanTax question first, because it's very easy.

That in itself might be an issue too. 

To make things even more complicated, I could possibly have roof issues, which means more $$ spent that I won't earn.

I am a real estate broker (specializing in multi family) and an investor in the Cincinnati market. 

I also would not limit by education although we do see it a little locally where some rentals will not take undergrads only grad students and it doesn't seem to be an issue. 

I had issues with the tenant and we went through a long eviction process.

This is not only to make sure that people are taking care of the property, but this is also to make sure that tenants aren't overlooking issues that could be addressed now that cost way more later.These can be minor roof leaks, gutter leaks, mostly to do with water penetration.