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.

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.

If I were you I would look at both and buy based on, in which property category you could find better deals based on an objective return such as IRR. 

Property owners must be given the opportunity to object to the budget. 

If you end up in court, and if the other side's attorney is an experienced trial attorney, they will object if you try to testify about the before and after values of the property.