Working with a great broker can also help as they will know how best to represent your interests and play the game.

I recently have connected with investors who are interested in assisted living facilities, with the play of unlocking government funding, not sure if there's similar opportunities with SL facilities.

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.  

Play games.

There’s no real reason to jump into another market unless your goals shift and your current market doesn’t fit anymore—or if the market itself stops producing the results you need.Mastering one market and squeezing every opportunity out of it is a much better play than spreading yourself too thin and getting half-baked results in multiple places.

I look for density plays that can be executed in an infill setting.

I meditate for 25 minutes, let out my dog, make my coffee and then play piano.

This cycle has played out numerous times:Mobile Home Park Residents Lose HomesMidfield Mobile Home Park Residents Lose Court BattleLoss of Another Tempe Trailer Park Highlights Lack of Affordable HousingMobile Home Park Residents Face HomelessnessIn an effort to preserve our country’s affordable housing, it is our duty as community operators to keep Lot Rents in line with the market rate.

Hi Robert,Given you are looking to buy another rental (long term), a cash out refinance on the existing property would be a good play here.

Retirement accounts are designed to be invested passively so when the IRS sees you running an active business in it, to level the playing field between retirement accounts and other business the retirement account incurs UBIT.