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No emotions just business.

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

ESP if you are planning to lowball, an agent might be more reasonable to discuss with (seller might get emotional and offended with your offer).

Motivation is an emotional thing.

Follow her basic guidelines and don’t make any investment decisions on hunches or emotions.  

Under federal law (ADA and FHA), true service animals and emotional support animals are exempt from pet fees, deposits, or rent, but the tenant must provide proper documentation if requested.

If you have someone in MN you trust to manage the place that is one thing, if you don't it kind of answers the question (not that you couldn't find one).Renting out homes which you are emotional attached to can be quite difficult when tenants trash them (which will eventually happen).Best wishes

We were trying to buy a loan that was in default and the current lender was emotionally attached and has it listed for over $2M when comps are $1.5M. 

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.