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. 

Then you have someone who understands the investors goals well and the technical experts really working together effectively. 

Select accounting and bookkeeping firms have access to software like Quickbooks Online at a discount, and a few of them even pass those discounts along directly to the customer! 

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

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

Most alternative investments work just like pretty much all RE niches work when deployed effectively.   

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.

This alone was most effective.

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

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).