You will counter more frame and stucco homes as you get into the outer areas of the Chicago MSA, while you will get a lot of high quality brick properties in the city and the surrounding suburbs (where I invest). 

Regarding final punchout projects, that may free up some of your time but it also gives you an opportunity to observe the almost finished product to help maintain quality control.

Often times, you can tell the quality of a market just by driving through it.

I was speaking with a lender who said LLCs might not be worth it and might actually be detrimental or my goals and speed of purchasing.

Does anyone have any recommendations for high-quality professionals in the following fields (preferably people who are themselves real-estate investors):1.

Your guests 'may' miss some of the amenities, but the hassle of fines for speeding/registration, the yearly fees, the calls from the admin office that your guests are partying naked in the street, or spread trash everywhere, just aren't worth it.

I would really like the help and will pay fair just looking for good quality work with good communication. 

It's low quality and needs a new roof and gutted to the studs, anyway.

There are better markets (Midwest USA for example) with good quality tenants , newer houses, better returns and not the headache of the new NY laws.

This thread is way too much rah rah full speed ahead.