Buy a new primary and rent rooms to relatives/friends/co-workers.

Illinois is tenant friendly state.

MF with many garages to convert to ADUs, parcel splits, full on development, coop/tic with the resources to handle financing challenges, etc.To raise money in this market as a newby will also be challenging unless you can get it from friends and family.

At that point I dont know investing would make any sense, I have heard scary stories I was thinking about short term rentals but that needs constant cleaning after guests and conpetition is very high my friend spent almost 200k out of pockets to buy a property for airbnb and he got 17 bookings per year....

One of my best friends thinks I'm rich and while I may have more than she does, I she was earning more than me for a lot longer (I make more than her now) but she spent her money on $6K vacations. 

To me, PML is a friend of a friend or an Uncle or a co-worker's father. 

If he gets put out he's just going to wear out someone else's welcome, which is probably a friend or family member and that's where he belongs instead of putting off his problems on you.

We have a real estate agent and investor friend, but not sure we’ll work with him.

Sharing your vision with real estate professionals, local investors, or even family and friends might uncover unexpected opportunities.

Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc.