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

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

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.

The play book as you described is an old one when it comes to marketing themselves nothing different than what the how to trainer do.

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.

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

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

If you understand the math of it all it should come very clear, the game is NOT best played (1) buying in all cash, (2) buying and sitting on a property for decades on end. 

It's a power play.