If you used them to purchase another rental/ use for another business endeavor...the process starts over. 

I'd start talking to her and looking for another place for her to live. 

So I'm a fan of buying in the path of progress from here since it's starting to expand outwards into cheaper neighborhoods.

Our team along with clients all are heavily investing in the area, and it is a strong place to start. close proximity to New York and New Jersey, paired with extremely affordable property/taxes and high rental demand make it on most people's radar.  

We are also planning to start spending winters in warmer climates... 

The list of property management suites at Capterra is a decent start, so long as you take their reviews with a grain of salt. 

If you are just getting started here in Chicago, house hacking is the ideal situation.

Finally, if you cannot find sold properties to compare within the timeframe or distance you can go out a bit to find properties to compare.This will get you started with finding values for residential 1-4. 

Hi Moshe,I too am looking to start my real estate journey.

It really helped us a bunch as we got started a year ago.