@Maria Teo An architect can only save you money on larger scale projects where IF they have the right expertise they can make cost saving design changes. 99% of the time they will not save you any money on your home remodel once you include their fee.Existing plumbing is grandfathered in I don't see how you would need to replace all of it to bring it up to code, you are probably mistaken.

The one revelation I gained from reading that changed the way I lived was something I learned in RICH DAD, POOR DAD: The home you own and live in is a liability, not an asset.

I agree that choosing a property/city you don't mind living in is a key factor, you will have a much better experience and long term success if you chose somewhere you enjoy vs purely chasing cashflow.

Putting an offer in is easy, it doesn't require all of the contracts etc, your broker just fills in a 1 page form and if it's accepted they email everything out.

Do you happen to have some sort of cheat sheet of a list of neighborhoods in Chicago and what class they are considered to be in? I

Anthony's suggestion of continuing to pay your regular rate of rent once you move in is a good one. 

We've got the management software and maintenance requests set up to proceed with self-managing but getting a new tenant in is challenging and time consuming to plan around with our our W2 jobs. 

Or military moving in?  I

I currently have two properties, one i rent out and the other I live in (I plan on renting it out).

I found that once I moved out of the market I lived in, I could pick the market that was best for the numbers I wanted.