@Tyler Garza keep it simple and play the long game.

Quote from @Sandra Morrison: @Shannon LeckingerI have STRs and LTRs - your condo will be possibly more of an appreciation play but you can’t pay bills with appreciation.

And that is really saying something because I invested a tremendous amount of myself and time into my small business and learning to play guitar and my personal recovery and growth as a person.

This clearly has nothing to do with laws, regulations or operating numbers but I do think it plays a large role in the decline of the market.

Income-based valuation only comes into to play once you get into commercial property (5 units and up). 

@Eric E.UBIT only comes into play in an IRA on leveraged real estate and running an active business.

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.  

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

Better play it safe and use a warranty deed instead.Also, later on when you sell your property, it will keep the chain of title cleaner for the next title insurance.Last but not least, a warranty deed does not cost more than a quit claim deed...

Rate and price play a big role in BRRRR.