You control the conversation, not them.Bottom line: Maintain control, play the long game, and don’t let emotions dictate strategy.

Self management works if you are local and can separate emotion from business.

The tenant lost but that wasn't any consolation for the worry, stress, and emotions they put them through.

off-market deals can sometimes be the most emotional situation you will encounter. 

They are only here to prey on your emotions and once they get your money, its on to the next sucker..

I've only held onto it because I have an emotional attachment to the area.

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.  

If you manage to pull a smile everyday and not get emotionally attached to any client or deal, you will be a rockstar and it will be a highly rewarding career.

They claim that the prior home did not give enough time and rushed the notice and caused emotional damage.

However that is more of an emotional investment IMO.