It may effect lease renewals.  

In this post, I'll share my thoughts on the value of a good property manager and how to select one.

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.

This is consistent with data from sources like Zillow, Redfin, and the local Santa Barbara Association of Realtors.However, when I go to "Pick Markets" and select Santa Barbara, the median home price listed is $620,000, which doesn’t align with what I’ve observed locally.

We are extremely selective with the deals we pursue and who we pursue them with.... which is why we have the track record we do.

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).

You might want to read our series about “How to Screen a PMC Better than a Tenant”, since selecting the wrong PMC is usually more harmful than selecting a bad tenant: https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processes

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?