Is there anyone who has personally worked with or is familiar with a great 203k Lender in the Chicago or South Suburbs area?

In case you aren't familiar with the term its simply buy,rehab,rent,refinance and repeat.what you could do is buy below market value properties, rehab the property which gives you more equity in the property,rent it out then  refinance it pulling out your initial investment which you  will use to repeat the process again and again..that is how some investors build a sizeable portfolio in a relatively short period of time.a couple of good multifamily deals might do the trick too.hope i was helpful

The easiest way to get this done the right way is to contact the local REIA and find out what attorney in town is investor friendly and familiar with SUB2.

I grew up working in the apartments and helping him with repairs, and upgrades so I have some familiarity with the buildings and general maintenance requirements. 

Using the aforementioned equity, acquire yet another multiplex and occupy a unit (much lower down payment and rent for owner-occupy) so I live for free/cheap s save for retirement on that acreage...and I can give retired parents a cheap unit to rent (helps them) and I have a timely and familiar tenant (helps me) and they're close by in their own space (helps everybody). 

I'm an investor in the area, primarily Jersey City, but I work in the area as well so I'm very familiar with the trends of each neighborhood.

I am not familiar with the in's and outs of the areas in Pittsburgh.

I highly suggest you hire and attorney or title company familiar with tax sale.

Familiar with wholesaling and assignment contracts.

They are usually people you already know who have money and they want to invest their money with you in what you are doing so they aren't very familiar with charging points or getting interest paid upfront at closing or those sorts of things.