We are doing some work in Hermosa right now and haven't had any issues so far!

You should do the bike ride but I know what you mean....I usually get distracted in Hermosa ha ha.

You'll definitely need a property manager that is hands-on and works in those areas though.The NW side of the city is going to be a longer-term appreciation play areas like Avondale, Irving Park, Belmont Creigin, Hermosa, etc.Happy to connect with you further Scott to talk through the city and your plan.

I live in Hermosa Beach, CA (land of the free) and use my Delta Amex frequent flyer card to fly down to Costa Rica in 5 and 1/2 hours flat and for free.   

@Alex TokmazeyskiyPortage Park, McKinley Park, Brighton Park, Bridgeport, Marshall Square, and Hermosa.

You'll find a ton of great Chicago investors here.I personally believe that you could make a house hack work....even with only $25k you could still get a 2 unit for $500 k ish in some of the neighborhoods outside of downtown like Avondale, Hermosa, Belmont Cragin, etc. 

@Michael FortierWith your budget/criteria, you'd be best served by going after the NW side neighborhoods such as Portage Park, Jefferson Park, Hermosa, Belmont Cragin, and Albany Park.

My approval amount for a duplex will be between $360 to low $400sTriplex $450 to low $500s dependingI have been looking in Avondale, Hermosa, Logan Square, Jefferson Park, Portage Park, Albany Park, and have even checked out Berwyn and Lagrange.

You will hear a lot of the same neighborhoods over and over again (Humboldt Park, Hermosa, Belmont Craigin, Little Village by Marshall Square, McKinley Park).

Albany Park, Irving Park, West Logan Square, Hermosa, Mckinley Park, Brighton Park, Bronzeville.