I own a two flat now in my name.

Well, since you can't rip the walls to look at framing, wiring, and plumbing, look at what you can see:1) Level of trim, appliances2) Finish carpentry or gaps in joints3) The flatness of floors and squareness of rooms. 

Is there a Chicago specific directory of average costs for things, like price per sf of replacing existing decking or flat roof replacement cost per sf?

If you are doing buy and hold then compensating a high flat fee amount might be more appropriate.

Flat roof? 

With a flat rate, you pay $50 (e.g.) whether you use no water or leave it on all day long. 

I'd go with Welcome Home Milwaukee, they have a flat fee model.

But it’s cheaper than the points and flat lender fees on amortgage, and you get to use the same credit lines over and over again for your flips or BRRRRproperties.

I was wondering if I can find and partner with local agents for the help on this.What I am looking for is:A) Access MLS APIB) Get property data based on MLS IDI am willing to pay for temp access in a format with a flat fee of a mix of percentage and flat fee of grunt labor of filtering through the MLS (as an assistant).Please let me know if you would like to help out and interest in it.

Of course I would rather be on a flat fee pricing model like Pricelabs and since I want to be like @Luke Carl (aka Yoda) when I grow up, might try Pricelabs at some point.