While I know this isn't a lot in today's market, I believe there are creative ways to make it work.I’m a former foster child who was declared independent as a teen, so I've been living with close friends that I consider family.

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.  

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@Dave Foster interesting, I didn’t realize this route existed.

Originally posted by @Dave Foster:@Glenna Wood, They're actually in conjunction with a 1031. 

There are larger fluctuations in emotions as larger sums of money go in and out of your account.

@Yacosa Foster in the Spartanburg area as well

We haven’t really felt the effects of it yet but I think that is mainly due to the timeframe it takes for them to process claims and emotions from the devastation.

It seems like you just really wanted this property so you let your emotions drive your offer.

Hard part with business is separating your emotions from it.