Are there resources I can look up to see if i can wait and enact new leases that include tenant paying utilties and what legal issues I may encounter there?

Eight of those members, each from a corresponding city council district, would be elected, while the mayor would select the ninth.State law restricts rent control only to apartments, homes and other housing units built before Feb. 1, 1995.

Even if it isn't specifically stated, there have to be some catch alls in your lease that gives you legal footing to evict the drug user. 

Does anyone in Chicago know the legalities around this?

Are there any legal reasons not to go with this approach? 

@Michael Weis - some lenders will actually get you as much as 80% depending on the loan program and whether it is recourse (i.e. you personally co-sign for the loan to your legal entity) or non-recourse. 

Would a HML tend to have the same restriction about a family member loaning me the down payment and the amount of time I had that money?

Are there any legal ramifications for running a business of that sort from a single family home? 

With my 9-5, I am part of a legal plan and have been for about 3 years.

If the lien was stripped it will still show in the land records... a title company would need to review the BK order as concerns the legal affect of the lien (or lack thereof).