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.

His problems are his own and there's no reason that he's telling you about them. The whole towed car thing where you offered to waive the late fee if he showed the bill is a reason why he's taking advantage of you. You're too nice.

Today, you start the first step of eviction for holding over in your area. If that first step is you providing some sort of notice to vacate (30 days, 60 days, wahtever it may be), do that. You might be able to find your area's laws online. If not, you need to find a lawyer.

Last thing to worry about is if he gets mad or not. Who cares? You can be professional and cordial, but still firm and following the law. 

Start the process to get him to vacate. Check your laws. If you've asked him to vacate, you may or may not be able to collect rent for following months that he is "holding over".

Just don't waste time. Start today.

I care if he gets mad because he may intentionally damage the apartment or the building on his way out which could cost me a lot of money...  I want to do this right without him creating more issues.

Do I need to give him 30 days from today to move out or can I tell him he needs to leave at the end of his lease term (May 30)? I never formally wrote anything that agreed for him to stay longer other than a text message and that was before he was late on his rent payment. Do I still need to go to court and go through the whole evictions process if he doesn't move out by the end of the lease (May 30 or 30 days from today whichever applies)?

First, you need to speak with your landlord/tenant attorney about the exact process and timeline in your state.  IL is a tenant friendly state.  Here in CO "30 days notice" means 30 days before the next time rent is due.  If you agreed to extend to June 30 you're probably stuck with that.  Its too late to give notice for May 30.  But you may be able to give notice that he will not be extended past June 30.  Speak with your attorney.  If you don't have one, today's the day to find one.

Second, making a tenant mad and having them damage something is the risk we take as landlords.  Could happen.  Probably won't.  You can't be intimidated by the possibility.  If you truly are, you need to sell or hire a property manager.  This is just part of the business.

Finally, his car being towed is absolutely irrelevant to you.  A response like "that's too bad, but the rent is still due" is appropriate.  If his car was towed it was most likely illegally parked.  In any case, his problem, not yours.

@Izabella W. I understand your fear of him damaging the property out of anger, but that is beyond your control and you're just fearing the worst. It is quite possible he will not damage the place, even if angry with you.

And even if he does, what's done is done. What are you going to do? Just let him stay there if he threatens to damage your place? And then next he doesn't have to pay rent because all he needs to do is threaten you again? 

To be direct, your fear is irrelevant.

It's too late to give him a 30 day notice that gives him until 30 May being that we are already at 09 May 2018. You need to send your notice for 30 days out of the day you write and send the letter. If your area requires certified mail, you do it that way. If your area requires posting it on the door, you do it that way (and take a video/picture). If your area requires multiple ways of sending the letter, you do it all.

I do not know if you'll need to go to court. Again, you must look up your area's laws on this situation. Assuming your property is in Chicago, Google "Chicago Eviction Services". Lots of results come up, including "Kick 'Em Out Quick".

Unfortunately you can't come to BP and expect people to give you step-by-step instructions on how to evict properly. You *might* find someone truly knowledgeable, but your best bet is to again, find a professional service/attorney to help you.

You need to learn your laws now so that you're not scrambling again  when you have an issue in the future. Do not wait for problems to arise to learn your local laws.

@Izabella W. At this point you need a property manager. Also start the eviction

Continue the eviction process you started with the notice. He did not satisfy it by not paying the late fee. Do not accept any more money from him.

Thank you both for your input @Nicole A. and @Jon Holdman .  Jon, it is especially helpful to know 30 days may not really mean 30 days; I'll find an attorney and will confirm for Cook County, IL. I've only been renting for 5 months and he is my first tenant so I don't know everything about how to handle every situation but I do appreciate your feedback.  I have a feeling he is planning to "live out" his deposit. 

Originally posted by @Max T. :

Continue the eviction process you started with the notice. He did not satisfy it by not paying the late fee. Do not accept any more money from him.

Great point! 

@Izabella W. Max might have a great point, but seeing that he is from PA (and not Chicago), he may be giving you suggestions/info that do not fly in your area. Some areas make you start the eviction process all over again if you accept any money at all (rather than only accepting a full payment).

I can not stress enough that you need to ask these questions to a local eviction attorney rather than BP members from all over the country (and world).

If he wants to stay, he will stay long enough to burn the security deposit if he decides not to pay.  There aren't too many states that you can get through an eviction in under 30 days.  We always go by the lease and if there is a balance to be added like late fees and such, we add it.  Getting into negotiating on fees ends up opening a whole new can of worms.

Your responsibility as a landlord is to learn ALL your state landlord tenant regulations before you rent to your first tenant.  Learn them now before you proceed any farther.

Once you give notice to non renew, based on your state regulations,  there is no more you can do until the first of June. If on the first of June your tenant does not pay rent you issue a request to pay rent. This will begin the eviction process. If he pays June rent there is no more you can do till the 1st of July. If he is not out by that date you then begin the eviction process.

It is critical that you do not make any exceptions to this process or you will extend the time line and lose more money. Hire a lawyer immediately if you do not know what you are doing.

Hard to say exactly what to do because states are different but I personally would get the legal eviction process started and follow through. After he's gone I'd get rid of the condo with the unreasonable association.

Thank you all for your input and advice.  I contacted an evictions attorney and found I have two options (I will confirm this with another attorney) to either just send him a notice to vacate or to try to go after what he owes along with getting him out.  Some lessons are learned the hard way... I will stick to my requirements next time and collect a higher security deposit.  No more trying to understand people's situations and trying to work with them.  

@Dick Rosen , unfortunately in my area, most condo's don't allow rentals and if they do, there are usually move in/out fees.  This association originally only collected fees resulting from a sale but got clever when they had an issue with another owner's tenants moving in and out without any notice and resulting in damage to the building.  I'm not opposed to the refundable fee because I believe whoever causes the damage needs to pay for it, so if it's my tenant, it should be my responsibility...

@Thomas S. - I will send him the 30 day notice to vacate now and will wait until June 1st to see if he pays, chances are he will not.   At that point, I will get the ball rolling and will hire an attorney to handle it.

Originally posted by @Izabella W. :

Thank you all for your input and advice.  ...I will stick to my requirements next time and collect a higher security deposit.  No more trying to understand people's situations and trying to work with them.  

Izabella, I would be careful about collecting "high" security deposits in Chicago.  There was a thread recently where a new landlord in Chicago was fined an obscene amount that was tied to a high security deposit.  Apparently, Chicago/IL landlord law requires regular payments and/or accounting of interest earned from security deposits, and failure to follow through on that can result in a fine of treble the amount of the security deposit.  Bottom line, the larger the security deposit, the larger the fine to the landlord.

A couple of Chicago-area landlords chimed in to add that they don't collect security deposits at all -- that they charge extra fees or do something else to eliminate the collection of a security deposit .  Search the Chicago forum and prepare to be horrified by that thread.

Here's one, but not the one I was thinking of: Chicago Landlord Returned Security Deposit, No Interest

Good luck,

Randy

Originally posted by @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.

 Is this in the city of Chicago?  I'm a landlord in Chicago...in general, I try to get bad tenants out at any opportunity that I can.  I have one right now telling me they want to move out and I'm totally okay with them leaving before their lease expires because they suck as tenants and I'm ready to be done with them.   

If you switched to a month-by-month lease, I believe you need to give a full month's notice.  And that is based on a calendar month.  So if you give them the notice on May 11th, that means they're to be out on June 30th.  

Another development, he hasn't replied to me since this Wednesday and today sent me a text with another story apologizing for not responding and decided to send the $50 late fee (which I received).  Other than the recent stories, not being responsive lately (he does work 12hrs a day, I know this for a fact), and being late on rent in May, he does not cause any problems. After that text today and his willingness to pay the late fee (I thought I'll never see that $50), I'm confused as to what to do with him. 

@Jeff Burdick , the condo is in Chicago Ridge (Cook county but going through the Bridgeview court system). I was planning to serve him the 30 day notice to get him to move out by June 30th but now am not sure.  Have you gone through an eviction in Chicago? Can you recommend an attorney or an eviction specialist?

@Randy E. , so far I'm only collecting one month's rent as a security deposit but when I did the research, I remember I could collect more.  As for the interest, I do remember reading the statues that it only applies to landlords with 25+ units (which I do not have, thank goodness) and if the tenant has leased for at least a year.  I've been reading some horror stories on BP which made me think about collecting non-refundable move in/out fees but the area where my apartment is located is probably a C neighborhood and most prospective tenants don't want to pay any non-refundable fees (it's hard enough to get them to pay for the credit/background check). The joys of being a landlord :) Thanks for bringing up this point, I'll definitely refresh my memory before making any changes and read the posts in the link you posted as well as others as you mentioned. 

"I'm confused as to what to do with him."

I would give him notice to vacate. He is a flake and will continue to be a problem. He is not trustworthy.