Am I legally allowed to increase his rent a little to cover the extra water usage? 

It is a solution in some cases but fees tend to be heavy to buy into them.No legal advice given.  

This is a legal question, so I cannot give you legal advice, and will not.

Do not rely on it as legal advice.

What is  the legal ramifications is in Chicago for personal property?    

I don't want to get caught up in some legal issue.

I'm not a BK attorney and this is not legal advice.

Lawn care/snow removal, pest management, Legal, accounting, other admin costs, to name a few.I am not trying to discourage you from pursuing this property. 

Renting out space in ones primary residence (and more) is legal provided that one adheres to the law that recently passed.

If this occurs, and the tenant wants to get their account in good standing, they must pay the late fee as well as any and all legal fees associated with the late payment.In our experience, this has significantly reduced late rent, and it gives the tenant the feel of a very rigid structure that will be less interested in pushing in the future.When we have bent on this in the past, it seemed to have created a never ending problem of late rent payment and our management company always begging for rent.If they don't actually want to pay the rent, then starting that eviction ASAP will save you a ton of money and rent loss.