If you have 100k of cash in the bank, how would YOU utilize it to yeild most cash flow/return. i'm considering all startgies, but essentially it depends on the deal and market. however, i''m focused on cash flow. 

It depends on the loan type and lender.

Im open to either DSCR or conventional Timothy really depends on the terms.

A lot of options and it depends on your goals.

Not 100% true, but that's what I see after 20 years.I think it depends on what you want to do though. 

This really depends how much you have invested on whether or not it's worth it and how much depreciation recapture he would be subjected to 

I suspect what TV you offer will largely depend on the nature of your rental.

Depending on the contract negotiations, the buyer will likely want title insurance and may ask for you to pay for the premium, which is calculated at as $5.75 per thousand dollars of the sales price up to $100,000 and $5.00 per thousand dollars of the sales price thereafter up to $1,000,000. 

Chicago's market varies, so $500k-$600k might get you something nice, depending on the area.

Theres also many local real estate meetups depending on how far your willing to drive where you can meet other like minded people and network to learn from them as well.