My budget is probably no more than 375K, but am open to 1Br's as well.  

Whether that be starting the side hustle of real estate investing, or finding a new job, but, personally, I would not suggest you leave a well paying job until you have started down the path of real estate investing on the side.

The project went so well my friend went 50/50 on a second multi-family in Berwyn a block from the Metra.

The current rents are well below the medium for the area.

Well, I guess actually reading the Due on Sale clause is in order: :-)"18.

As @Charles Carillo said, you can make the most of that time, but most people just waste the 4-5 years and then end up doing something unrelated to their degree field anyway.Maybe look into a Trade School, like an electrical one....nice clean work that pays really well.

It almost never ends well. 

Ive spoken to PM's down there as well as Clayton himself.

So I am looking to invest with HomeRoom as well.

I'd leave a message and tell them since they have not responded to your multiple inquiries and you have not received the rent they collected in a timely manner, that you will be contacting your lawyer as well as the licensing board to file a complaint.