I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

Would definitely recommend finding a partner who can help walk you through this if you decide to move ahead. 

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Does anyone have recommendations for a contractor for an almost full gut property in Rochester NY?

Quote from @Brian Hill: Do anyone have a recommendation for a San Antonio Real Estate Attorney that deals with creative financing and title work? 

Once you sign up there’s a ton of other systems (Freedomsoft, Prycd, Mailers, LLC, phone lines etc)he recommends that you get in order to do his program successfully.

I have never pulled a permit for a water heater swap, know no one that has ever pulled a permit for a water heater swap, ever seen or heard about one getting red tagged for no permit, and have never had a plumber recommend getting a permit.

First, I recommend you understand the market.

My recommendation is before chasing all these real estate deals is to go earn and save some money so when a good deal comes a long you can take action and move on it. 

I strongly recommend getting involved with your local REI meetup groups so you can work out your pitch with help from other landlords.I hope this doesn't come off the wrong way without tone or facial expressions behind it.