I let them run to the end of the year as m-t-m, then send a rent raise letter, usually for $25 or $50, on or about Nov 1, effective Jan 1. 

There are more effective ways to accomplish this.

If you only plan on owning 2-4 properties, then there's really no harm in self-funding them unless you know a better, safer way to make more than the going interest rate on that money (most investment mortgages right now are about 7%, maybe effectively 5.5-6% after taxes depending on your brackets and tax structure).

@Sam Alpha  I think this thread is effectively over. 

Read: The millionaire real estate agent; Hyper Local Hyper Fast AgentWhat are some effective ways to network with individuals at all levels?

Or because they don't want to be the bad guy.With closing on Dec 4th the issue is that your 28 day notice will be effective Dec 31st and your tenant has until Jan 31st to vacate.

What's the most effective means of dealing with this issue?

A good property manager can guide you in selecting properties that will attract a tenant segment with a high concentration of reliable people.Access to cost-effective resources for renovation and repairs.Lease terms enforcement.

Its much more cost effective to outsource things like skiptracing and direct mail.

Eliminate debt, establish a budget, and save.