In late 2021 my wife and I both found jobs in Chicago, bought our second property (also a condo) there, moved in and had our first kid there.

Great pricing and the most accurate data that I have found.

@Matt Devincenzo Yes, we were the ones that found the homes.

I've found that around your price point (mine is similar), about the only things avail are condos and town homes in my price range.

We did not do our due diligence regarding the HOA rules and found out after purchasing that we are not allowed to do short term rentals. 

I have a mentor whos been investing in the area for 10+ years and he's only found 2 flips this year.

There are no tools that I have found that accurately capture rent trends, its more so just looking at what current rents are in the market and having the experience to understand how much rents have gone up4. $20/month if basic.

I’ve found that as long as they’re somewhat insulated and well installed the color won’t matter.

It has good rent to price ratios but taxes are on the high side and I have found that I need to be diligent with oversight of property managers who run operations; especially with lower income tenants.

@jessica cheung I found the oxford house I was looking at listed on zillow.