Personally I've been a fan of the suburbs and sub-markets for a while just because of the trends I've seen with folks in my generation. 

I’m leaning towards a business degree of some sort but want to see what other members who have already been in my shoes have gotten and how that degree has helped them out.

I usually am not a fan of this, however 2 had been there for 20 plus years.

The first thing I would do were I in your shoes is find a local, experienced real estate investor who might need someone to do grunt work for him. 

Hey Corey, I am a big fan of house-hacking.

A lot of people wondered if the housing market would fall off a cliff when the COVID really started to hit the fan, but obviously it didn't.

If it really hits the fan for you then you can always file a a disaster relief fund App or apply through Chicago Small Business Resiliency Loan Fund.As far as needing cash for college do you already have a SallyMae student loan? 

The bathroom will have a fan installed and new vanity and paint.

@Kyle Hines I don't mean to sound like a downer but I was not a fan of driving dollars.

I am a huge fan of following up on properties like this after they've sat for awhile.