For most investors using this strategy (myself included) maintaining decent Cash Flow is still an end objective.  

If you are incapable of separating your emotions from a material object you will be incapable of making a logical rational decision.Personal homes are a liability, sell it, keep it, what ever you choose does not matter if it no longer a investment.  

I feel like I've maintained an objective point of view throughout and have taken steps to learn how to analyze properties without the emotion. 

If your objective is to cash in on some of your investments and you have a good plan for the money you'll receive by selling - maybe paying off some debts, take your spouse on a nice vacation, etc. - then I say do it. 

Always beware the shiny object syndrome. 

Separate emotion, evaluate objectively.

Think in advance some of the objection you might get and be ready to answer.

If you are looking for quantity it's not a bad area to work.

This may be one of the reasons.2) If you know tenant's social/case worker, with tenant's approval (provided current seller doesn't object), you can speak to them to get an understanding of the tenant etc.  

Also keep in mind the objective of government funded loans (specifically the VA) is to get former service members into home ownership.