Investors & overall market feasted on low rates, you got your stuff together during that time and now are seeing how cycles play out.

Talk to a CPA to see how each scenario plays out.A 401K continues to grow in value, but what do you live on? 

There may be other issues at play here that have little to do with a lack of experience at real estate tech platforms. 

I’m all done playing those games.    

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.  

This is a very different space than most folks here on BP play in from what I have seen.

Do number, size, or area of investments owned play the biggest role in that decision? 

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

Quote from @George Skidis: Not an attorney and don't play one on television.

Vrbo and Airbnb do not play around when they see you taking direct bookings from guests who found you through their platforms.