tenant refuses prorated rent, hasn't changed utilities - chicago

[Jay Garrison]

Hi,

I have a tenant that moved in on August 16th; before she moved in I sent her a text telling her I would prorate the rent in September and that she had to pay a security deposit + one full month's rent to move in. The lease she signed stated that rent was due on the first of each month and penalties for non-payment began on the 5th.  

Two days ago I texted her the amount that she would need to pay September 1 is XX dollars and she balked, telling me she didn't know what prorating was and had expected to pay each months full rent on the 16th of each month, which she had "always done before". I pointed out to her that I had not only texted her about the prorated rent, but I had discussed it at lease signing and the lease said rent was due on the first of each month. She said she didn't have all the pages of the lease; that i only sent her the first page (with our signatures, the rent amount, lease dates, apartment inhabitants, some other info) however she did sign page 1 and initialed pages 1 and 2 (but not 3). The only page that required a signature was the first one.

She further stated that since I texted "pay prorated rent in September" without a specific date in September attached she was within her rights to pay on the 16th. I spoke with an attorney who asked if I really wanted to go to the mattresses over a half month's rent, and that eviction was messy, just let it slide. I should mention here that I live in the 3 flat where she also lives, so most of the rules about RLTO don't apply to me (only buildings of 6 units or larger apply)

From the RLTO
(a) Dwelling units in owner-occupied buildings containing six units or less; provided, however, that the provisions of Section 5-12-160 shall apply to every rented dwelling unit in such buildings within the City of Chicago

5-12-160 says no lockouts, threats of lockouts, seizures of property, etc. 

Then, earlier today I noticed she left the lights on all day (again) and got an inkling to call the utility companies and lo and behold, she hadn't changed the electricity over to her name. I had to remind her about the gas on the 22nd. I am a newbie and it looks like one slipped through on me, but i do have a security deposit from her and I know it is tougher to evict someone during the winter, so I am considering my options. She seems to be trying to get away with as much as she can, and with all this just two weeks in I have a hunch this will get messier.

I had intended to accommodate her wish to pay on the 16th, but now with the utility thing I think she is trying to game me. Thoughts? Sorry for the long post