I am trying to glean as much info as possible to develop a good solid strategy.Thanks for reading!

I have an associate who would like me to invest in HIS project, which I've never done - I've always been the developer, not the lender. 

There are still rules that need to be developed, but based on this being in Cook County, I highly doubt those rules will favor landlords in any way.Now on to my opinion soapbox.

Again, something to understand as you develop your strategy. 

I found a deal where new development is happening, $250k homes are selling on a street where properties right next door are valued at $50k.

As an example, if you like short term, high risk, with the chance of higher returns, you may want to invest in a development project or MH bridge debt.

You can always develop your own, buy why not take what has already been used multiple times and has been legally tested.  

Larger deals are more asset based but experience becomes a factor so you will need an experienced operator on the GP side and or as a KP.A commercial loan under or near 1M is considered a small commercial loan, and I may struggle to find a loan provider.Smaller local and regional banks are great for these loans but they will be looking to you for qualification and person guaranty.

I am not buying, buying, buying, so the changes come with appreciation (which are pretty good, since I've been buying next to developments). 

My sharing openly and honestly about who I am, my club members have come to appreciate the vulnerability I share and it develops a sense of trust and intimacy in a relationship.