Craigslist, Zillow, local property mgmt company, etc) because not one of these sources by themselves is entirely accurate.Specifically, with regards to Rentometer, keep in mind that it does not even factor in how many bathrooms a home has, the condition of the home, size of the home, or even type of home (apt vs SFR).

Wife and I are late 30s with two little kids and the $5k could fix both bathrooms in the rental we want to sell.

Per the link below, I'm seeing that in a "sleeping space" that the ceilings are permitted to be 7' (or less, for a bathroom):https://www.map-strategies.com...However, the chicago code says the height should be 7' 6":https://chicagocode.org/13-64-....So which is it?

The next stage would be to install sheetrock on walls and ceiling, waterproof bathroom walls and install tiles, finished flooring, new kitchen cabinets and appliance, install bathroom fixtures.The problem is time. 

I've converted the laundry room into a bathroom and can easily add 2-3 more bedrooms if needed, but not sure I want to go that route.

Eliminate all popcorn ceilings, repaint everything, new flooring throughout, renovate bathrooms, add a bathroom, renovate the kitchen, improve outdoor living, improve curb appeal, and believe it or not, make the garage exceptionally nice.

Eliminate all popcorn ceilings, repaint everything, new flooring throughout, renovate bathrooms, add a bathroom, renovate the kitchen, improve outdoor living, improve curb appeal, and believe it or not, make the garage exceptionally nice.

If you can value add with an ADU, add a bedroom, bathroom you could force appreciation.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

Changing the current layout from a 3/2.5 to a 4/2.5 while enhancing the master bedroom into a master suite with huge walk-in closet and bathroom.