I have read through many of the chicago STR ordinance website pages but I can't seem to find the answer to my question. 

You may hire licensed contractors, but most-often the workers are illegals from three countries I will mention (Honduras, El salvador and Guatemala) and attorneys are constantly sending workers emails telling them to visit their office because there just may be something they can sue you and there boss for.

I think being Free, and living off the cashflow of the investments, and not being tied up at a certain location for a job, and the family willing to move to other cities and states to check out other possible places to live make this possible.My wife and I are thinking of doing this, we just bought plane tickets, rented car and airbnb to visit another state.

Web based3.  

Not looking for sympathy and want to say that just like getting horrible advice from brokers, I went to the emergency room at 4 different hospitals 5 tmes, went to about 12 doctor appointments to 4 different specialty doctors, went to 4 different chiropractors and remember this:Just like what I said about getting bad investment advice from brokers the same advice has been applicable to every hospital, doctor and chiropractor I visited.

I also know that the lower prices to be found in NY have a lot to do with there being older buildings, higher property taxes, tougher neighborhoods, less appreciation, etc. which I know I will need to incorporate into deal analysis accordingly and understand the risk of.Summary: I feel that with having to put 20% down (FHA loan house-hacking is pretty much out of the question in NYC due to the astronomical prices here), buying a property in New York may be more attainable with my current savings and would allow me easier access to visit the property, however I don't think I could afford the quality of property I would like (close-ish to turnkey) in Florida.

If you do decide to do a flip, I would visit your local REIA (real estate investor association) and look for someone there. 

@John Underwood I used to print out google maps and as I drove over a street I would color it in red until all the streets I wanted to visit were filled in with red.

Is there such a feature on BP or should I just set up a FB page for the project?

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it.We have a 12 page management contract that we've added our real experiences to over the years, with the intent of protecting both us AND the landlord.