Props to you for having the foresight to invest in Chicago when your daughter moves up here.Some of the neighborhoods I like that may need some TLC and be at a lower purchase price would be Archer Heights, Brighton Park, McKinley Park, and Little Village. 

A good chunk of our state lives in small villages only accessible by road where the cost of living was astronomical before inflation.

I definitely like those Southeast areas around Brighton Park as well such as Mckinley park, back of yards, and little village.

The ratio between new construction prices vs rental rates in Central Florida is healthy in the targeted areas (Marion Oaks, Villages, Silver Springs Shores, Belleview) and the goal would be to find a 1% rule deal i.e buy a Duplex for 300k and have it rent for at least $3,000 a month.

My clients have been pleased with both Jesse Marinez of One Village Property Management and Debbie Rogers of Rogers Property Management. 

Type your city/village name in and scroll through the details.

My clients are seeing the best value in Southern Queens - Jamaica, Richmond Hill, Woodhaven, Ozone Park, Queens Village, etc - and Southern Brooklyn - Canarsie, East Flatbush, Cypress Hills, Brownsville, East New York, etc. 

Areas like German Village, Hungarian Village, Southern Orchards I believe Southern Columbus is defined by a couple trends1.

I usually invest in the east english village area or harper woods message me if you need any pointers.

Little Village (near Lagunitas at 2607 W. 17th St), Bridegeport (Halsted and 35th near Nana) McKinnley Park, Bronzeville, Brighton Park and Gage Park are all communities that may be more attractive to Gen Y (until they have children) gentrifiers because of low cost of rents and the ability to purchase property and pay off student loan debt at the same time.