At the moment I am calling title companies to find out who will be the best fit for me.

Just like you stated the other agents have me doing all the legwork sorting through all kinds of properties that don't even fit my criteria.

For some reason if the STR doesn’t work as you thought it would than you walk away minus any small money you  may have put up for the option.It would be considerably less stressful than having bought the home and now being in a situation where you want out of the home .

You can also go to the Chicago City Hall, 9th floor, there easy permit desk, you can ask them about the process, if you are lucky and walk up to a nice person he/she will help you. 

-After expenses my cash walking away from deal was 137K.

What happens there is a mishap that buyers walk away or lender not funding no fault of buyer or agent?

I plan on getting rid of/painting over all of the brown wood paneling in this house, replacing all of the flooring, rebuilding that small deck off the master bedroom, some minor landscaping, replace the garage and front doors, replace exterior door under deck, replace all light fixtures, update the kitchen (keep cabinets and paint them white with new pulls), paint the outside and add siding to the right side and back of the house (front and other side has siding already), change out bathroom sinks and countertops, paint all the cabinets in each bathroom, perhaps install walk in shower in big bathroom that has the tub.I plan on keeping the marble flooring in the entry way and try not to replace any windows.

Secondly, have a General Contractor walk the property with you to give you an estimate.  

Apon leaving the property, the man living there walks up to our car and lays some serious news on us.

(THEN, of course, wholesalers who have to buy it EVEN cheaper because they need to fit in their margin in addition to selling it cheap enough for #6 to buy it!!).