Is this legal ? - I have a Non Paying Tenant on a month to month

[Rema W.]

Quick Question? I have a tenant who has failed to pay their September rent. Their lease waives the 5-day notice to vacate requirement.  Technically, I can post and schedule an eviction date today. September Rent was due on the 1st. I've communicated that their month-to-month lease won't be renewed and they need to be out by the 13th of Oct. 

Question: Can I pursue the eviction and non-lease renewal paths at the same time?  See the options below. 

As I understand it, eviction assures that the property will be vacated on the court-ordered date (Oct. 1st) while waiting for the non-lease renewal deadline to occur presents a situation where I could be out of rent for two months (Sept and Oct), while having to wait until November to make ready.

FYI - I'm managing these remotely. 

Option 1) If I evict, it'll cost me court fees and agent/property mgmt. representation. (e.g. $250) For discussion, the eviction date could be scheduled for two weeks (e.g. The 1st of the month)

If I evict now, I'll be out of the $250, but I'll be assured that the property will be vacated on the 1st or shortly afterward.

Option 2)  I've sent him/communicated this week the notice of non-lease renewal, with a vacate before the 13th of the next month (Oct. 13th). To me this covers me in the event they pay September's rent. They still would have to move. 

If I don't evict and assume that he'll vacate on the 13th of the month following the "non-lease" renewal guidance, he May Not leave, and I'll have to file thus putting the eviction date sometime at the end of the month Oct. (31st). In this scenario, I could be out of 2 months rent.