Kim, Jonathan and Andrew provide some good insights. 

CHA has a mobility counseling program for families to qualify for special vouchers that will allow them to move to mobility areas &  there's an incentive for landlords to accept these tenants - 13 months' rent on a 12-month lease.On the southside, the mobility areas include Bridgeport, Kenwood, Hyde Park, Archer Heights, West Eldon, Garfield Ridge, Clearing, West Elsdon, West Lawn, Ashburn, Beverly, Morgan Park, Mount Greenwood, East Side, Hegewich. 

Originally posted by @Andrew Powers:@Alexander M Stanton what are your concerns?

@Andrew Pokrzywinski Thank you!

Thanks @Andrew Freed, I'm on about 250 right now, but will skip ahead to that one for the next one.

@Andrew Freed Cozy is probably a good start and it is free.

There are only a handful of actual good ones though and @John Warren named a couple of them.Although Chicago REIA is a little more sales ish, Andrew holmes also provides good content and know his 

@Wilson Auyeung J Scott Morse, Andrew Gray or Anthony Onwuanibe.

Good luck, Andrew

@andrew powers The most challenging part about roomates was finding quality people.