I bought a tri-plex in North Park, San Diego 25 years ago. The rent when I bought the property was $300 each for the two bedroom units or $900 a month with a mortgage payment of $900 a month. Now I get $1600 a month for each unit or $4800 a month. So if you keep the unit and pay it off you will get a lot more then your think 20 years from now.
Historically San Diego RE investing has produced outstanding ROI. The RE market appreciation is likely how you obtained much of that equity. It would take years of Midwest cash flow to equal the profits from the last 5 years of market appreciation.
Trying to time the market is difficult and risky. It is like trying to time the stock market. Statistics show more people do it poorly than coreect.
Historically the best return would be achieved by keeping the property. No one knows what will provide the best return in the future.
I would be more than happy to help you run the numbers for the various scenarios available to you.
I shot you a PM, so don’t hesitate to reach out if you’re interested.