If you want to get your RE license and skip straight to a full time career, apartments may make more sense. 

Are their Rehabbers and Fixers that would do this as opposed to a straight assignment.

Ive always had a knack for business and it has led me straight here to BP.

The current plan is to go straight into a rental, then begin the process of home buying (primary residence) within a month or two of getting settled, knowing it could take several months to find what we're looking for. 

To get straight to the point, I'm currently living with my in-laws (not totally for free) & saving for a house with my fiance.

Roughly, 1/3 of the net proceeds...That's a straight rip off!

I would bring the current owner with me and have a face to face talk with the building officials and get it straight from the horses mounth with the current owner being aware. 

Right now my options are to buy 1-2 apartments at my town and this is the best thing to do for now and to add up to 3-4 Apartments/per year for the next years to come (3-5 years).If I was at Patra right now I could acquire 5-6 apartments with the same capitals that I will spend for 1-2 apartments in my town straight away with not so much effort.

Almost impossible to get a straight answer from either Air Bnb or the City of Chicago.

@Weina Shi Great question, but I dont think there is a straight forward answer.