Tenant wants to extend 1-2 mos but was late on paying rent

[Izabella W.]

I need some help/advice. These are the highlights... Tenant had bad credit which he explained (540-570); I wanted to rent the apt for the winter so I wrote a 6 month lease and explained we could extend if all goes well (lease dates Dec 1 - Jun 1). He qualified with income but only due to lots of overtime and gave me this story that he has an interview for a Sheriff position in a month (never happened).  Fast forward to today, he is "looking" for other job opportunities with better pay, he had someone staying with him part-time that he "forgot" to mention to me, and in general the communication has gone downhill.  In April he said he wanted to extend two more months on month to month (till August) and I agreed to let him stay one more month until July 1. Let's say he paid on time until May 1 and on that day he told me his car was towed in Chicago over the wknd and it cost him $880 to get it that Monday so rent will be late. The next day I served him a 5 day notice (he was trying to avoid me).  He paid on day 3 without the late fee ($50). He said he would pay the late fee on day 5.  I gave him the option to send me a copy of the bill for the towing to waive the late fee.  He did not pay and did not send me the bill and has generally become very unresponsive.  At this point, I think it is wise to move him out ASAP so he doesn't try to "live out" his security deposit or try to sell me any more stories.   Thoughts?

Do I need to give him 30 days starting today to move out? How do I go about this without pissing him off? What happens if I tell him he has 30 days to move out and he doesn't? Can I just go to the Sheriff and have him kicked out or do I need to go to court, etc? 

Another caveat is that this is a condo, association requires a move out deposit of $100 and move out dates for inspection. If neither is provided, there is a $300 fee to be paid by owner.  

Any and all advice is appreciated.