If so, you are not legally allowed to keep his deposit for rent if his lease has expired. 

Cozy.co offers rent payments online for no fees. check em out. there's a delay between rent sent and received but it's easy to use and my tenants like it.

If you want the word docs, we can provide those too but need to make sure you understand that any material changes should be done only under supervision of an attorney, and that adding clauses does not make them legal or enforceable.

BP is one of the best online real estate investment websites.

You should stay on track of educating yourself through books, podcasts, networking with others - offline and online.

Am I legally able to pull this off?

Its is a legal 6 unit building in Jackson Park. 

This was a vacant lot that was advertised online with a no reserve auction for $101.

My manager has basically said that we can either go after the money or the eviction and that her inclination is to wait until the end of the month and then if he isn't gone begin proceedings (to avoid legal fees) .Am I looking at this wrong when I think its best to get the ball rolling on the eviction now and stop the bleeding as fast as we can? 

(This is legal in our area because of our building class).