Make sure to study up on the rules and regulations that go along with it. 

Hello Alex,Hope all is well. learning the lingo of real estate comes with experience, it's almost like learning another language you can study words and definitions all you want but the best way to learn is through conversation with someone who speaks the language. 

I've studied RE a lot and I feel ready to do a career change!

I'm a simple guy so all of that is kind of "blah blah blah" a foreign language to me. 

My New Years resolution was to go from studying theory to connecting with experienced investors to better understand my options.

Go by the exact language in the lease.  

In addition, you will want to study the laws regarding rental properties in Chicago.

They study the qualities and attributes of people with a net worth of at least one million dollars.

@Amiee Baker, LU has 3 levels of membership: FFP at $500 (sometimes they have a "sale" at $250 - that's how much I paid), Challenge at $8K (or $10K - I don't remember), and PIG at $20K.For $500 (or $250) you'll get a 2-day seminar, one year of general QA with their member services, 12 case study/networking events (once a month, and you may continue go there after your membership expires), and a vendor list with some discounts.

Gives you some good tips on how to bullet proof your house to protect from tenant damage, inspections, etc... some basic information.As a cautious investor be sure to study the section 8 strategy very carefully.