Rebellious tenant continually pays $10 short rent, ignores notices. At my wits end

[C Rutherford]

Looking for more advice as I'm struggling to find a living solution.  I'm trying to manage and rent 5 units all by myself- which has turned out to be way more work than I imagined, and the money has never been particularly good.   In fact its been quite a lot of stress and long hours, especially lately.   

Part of the low money reason is I very quickly found that 5 units is all the deeper I want to get into property management.
Housing humans I have found is unpredictable.  They can be unreasonable, unfair, lie..... sometimes damage property or bring in pests--- and they don't stay- the continual vacancies and renovations are the biggest hit.
I can do this, but I just don't want to get in any deeper.    The idea was always to have a second business, but that just hasn't materialized and I can never get caught up.
I've also been at this for a number of years now, but seem to be stagnated and going nowhere.   I need to pivot, but haven't found a solution yet.  

Right now one of my immediate problems is something I've never faced before, and is unexpectedly driving me crazy..  
After vetting very carefully I ended up offering my studio apartment to a woman with 2 cats.     She makes a big fuss about them- even has a cat mat in front of the apartment, and on.    But I checked her previous rental and she kept it clean and took care of them, so gambled on her.
What I got was something totally unexpected.  

This woman keeps a clean apartment, takes care of her pets, that's all good.   But she pays short on rent.   She's done this three times now.   I've never seen anything like this before.

She continually pays $10 less than the stated amount on the lease.
Let me say first:
As an incentive, I give tenants $20 off rent if they pay ontime.  I've done this for years.   Surprisingly, this usually results in everyone paying on the 1st, and with my slim budget, its necessary.   It also makes a nice sales pitch when trying to fill vacant apartments.   The system works, and I'm OK with it.

The first month she paid $10 short, I told her if she got the missing $10 in by bank close on the 1st, she can get the discount and avoid owing $30.   $10 to save $30.  Makes logical sense right.
She went back to the bank, and deposited the $10.    All was good.

The following month:  She paid $10 short again!   Again I messaged her about it.   This is not the rent stated on the lease, and you need to make complete rent to avoid any late fees.
This time she tells me, its too late to go to the bank, I can deposit it in the morning.   Trying to be nice, I make an exception:  Okay, if you can complete the rent payment first thing in the morning, we'll still give you the ontime discount.  Even though rent wasn't on time right.    
She pays the $10.

My reward the following month for letting the rules go, was she didn't pay rent at all.
I usually message everyone on the morning of the 1st to remind them to get the ontime discount, they need to get rent in by bank close.
I message her.

"The bank is closed?" is her reply.  "Well then I'll have to get rent in 1st thing tomorrow morning!"
"No no, the banks are open, all 3 branches", was my reply.  I passed on the bank phone number.
"I'm so glad I checked with you.  Now you can complete rent ontime, and get the discount."

Bank closes, and no rent payment at all.
OK this is extremely weird.

So I call her, and explain about the ontime discount.
She complains about the tenants upstairs, saying they brought in roaches.   
"They told me they're moving out", was my weary reply, anticipating the mountain of work ahead for me, to renovate their trashed apartment.   The people upstairs are indeed, unclean.    But they have always paid rent, and I've dreaded the long renovation after they leave.... and so I've endured it.
"I'll have to keep my cats at a friends house until then" was her reply.  

My response was to immediately schedule a roach spraying, which of course I'm doing myself.
Set it for next week.  Sent announcement to all tenants.  I could not be addressing this faster right.
"What about the rent?"  I ask her
"Oh I'll pay that in the morning", is her reply.

The next day she pays rent, late.   But she pays $10 LESS than the discounted on-time rent, again.
I text her:  Please complete the rent, you need to pay $30 this time, as its both late and short.
She doesn't.

Finally, having no other option, I mail her the 5 Day Notice.  This is the notice in Illinois which states their lease rights can be suspended at the expiry of 5 days if they don't pay rent, standard fare.
Being nice again the 5 Day Notice- Incomplete Rent states:   If you pay the $30 by October 9th, there will be no late fee.  If it is not paid by then, there will be a $20 late fee and tenant will owe $50.

The 9th comes and goes.  She pays nothing.

I'm now looking out of 5 apartments, vital for my income survival.  1 is currently vacant, I am trying to fill.
The second, the roachy people upstairs, who have told me they plan to move out next month, which will be a massive ordeal to renovate clean and re-rent.
And this woman, #3.   I am up against the wall.  I mailed her the 5 day notice, saying she must complete her rent, and she won't.

Do I file for eviction over $10?
Then I may be looking at 3 out of 5 of my apartments, vacant.   Talk about stressful, right.
But if I don't do anything, this basically tells her she can pay less than the stated rent, from now on.  Which is a disaster in itself. Not to mention the other tenants may find out, and start doing it too.

What would you do?

[Drew Sygit]

@C Rutherford you are letting the tenantns train you!

Highly recommend you stop being so nice and run this like a BUSINESS!!!

1) Send 5 Day Notices when rent isn't paid in full - like clockwork.
- If you don't "start the clock" on the eviction process, YOU potentially increase your loses

2) Do a polite, but firm call the day before you send the notice to your attorney to file court case.
- Only allow MAX 3 days for them to make payment or you send to attorney

3) Do a polite, but firm call the day before court to see if they plan to pay to stay.

4) Once you receive eviction judgment, do another polite, but firm call to see if they plan to pay to stay or are moving.

5) Payment Plans: desperate people do desperate things - require the TENANT to put in writing specific days & amounts. Put these into a Google Sheet and be sure to add future rent charges (they ALWAYS forget to account for these!) so you can see how long it will take them to get current. NEVER tell the tenant the amount of payment you want as they will just agree so they can stay longer, but are unlikely to make the payment.
- Always require a current paystub or similar to document income to support the Payment Plan, else evict.
- Tenants serious about staying will cooperate, the majority will make more excuses:(
- Unfortunately, you will have to remind them the day before payments are do, otherwise they will spend on other bill or pizza.
- Do NOT accept excuse, "I will have to see how much my paycheck is to see how much I can pay you". This is BULL****, they all know how much their check will be! What they are really saying is, "I have to see how much I have left over after I pay higher priority bills"!

If you can't do the above, hire a PMC.