Originally posted by @Crystal Smith: Pilsen & Little Village are great areas to find multi units at reasonable costs near the loop.  

@Crystal Smith I like your answer...

No one has a crystal ball right?

@Andrew Bauer and @Crystal Salton Will do.

Just need to find where I hid my crystal ball.

You really only have to have one bank account as long as you are crystal clear with your book keeping with each series. 

One could credit the remaining folks for the deposit on file and return just the leaving tenant pro rata, but then you need a small check from the remaining tenants anyway to get the full deposit, and you never know how they have allocated or paid the deposit (or even if they are on good terms), and you rely on the kindness of strangers to return it to the leaving guy (so he does not ask you for it later).Either way, make sure it is crystal clear and communicated (I communicate it multiple times) to ensure a smooth transition and prevent problems; that may be key, get the fuzziness out and make sure no feathers are ruffled.

Thanks Crystal Smith Our property management company is recommending sending the tenant to collections and then filing for a judgement.

Someone who doesn't mind guiding me through the process and is crystal clear.

Crystal - check my blog  - How to Green Your Green #3.