Might be a little bit down the road for me, but that is for sure dream that will come true...One Chicago's best features is the lake, which I'd like more access to.

@Andy Ptak when jumping into the industry you have a few choices:1) Start at the bottom2) Leverage your experience to convince someone to give you a chance3) Decide between:--- Big companies who will usually start you at the bottom--- Small companies that will more like to a chance on hiring you for an above entry level position.

Stay patient, something will come up that makes sense.

Not one single strategy will work for every property. 

Just do 10 of those per year and you will make 300k per year.

Now this does create a chain of liability where you (the employer) is liable for any misdeeds by the non-licensed employee be it by intent or ignorance, it will not matter. 

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

It was on the market for a long time because it didn't qualify for conventional financing will it being unlivable. 

One never knows whether an area will gentrify but chatter on the street is money is flowing in the South Shore.

They might be willing to give different terms especially to a high net worth person that they can likely make money on cross selling.