Also keep track of when you call the city and when he gives you a notice of non-renewal.

I would give notice to non renew and find a good tenant that can afford full market rent.

Is it smarter to do a 6 month lease to get off winter cycles and then renew 1 year+ starting from spring?

After speaking with some property managers, I'm realizing they really know how to tack on the fees... 10% (expected) of all revenues, 1/2 months rent for first lease, $400-500 for new leases thereafter (which most will be), $200 for renewals, $500/unit cancellation fee, no late fees passed along to me owner, some have $50/unit vacant fee! 

This year, I decided not to renew the lease when it was up because the tenants had started wracking up unpaid utility bills and had been late with rent several times.

They will then fine the owner of record of the car and wont renew any tag or drivers license of the owner till the fines are paid

I’m about to be at the 3 month mark prior to their renewal and want to present a new lease.

Assuming she is M2M or at the end of her lease I would give her notice you will not renew her lease at the end of October. 

Some leases auto renew for 1 year.

I sent her a certified letter yesterday saying to avoid foreclosure or any other action she must provide proof of insurance on or before October 12 & if not renewed I have no alternative but to FP a policy.