@Jason Brown - I'm a CT based investor, flipper, and property management company owner.  

The big pros are the strong job market (lots of major employers), good population growth, and still-reasonable entry prices.

Not a strong argument ;-) I still had to pay off the loan to cure the DOS. 

Based on the knowledge and experience you have, would you consider this strategy if you had to go back at my age?

In the end, buyers would overpay for the actual property based on earnings.

If you’re open to exploring outside the Bay Area, markets like Milwaukee, Chicago, and parts of Indiana offer strong potential for flips and rentals.

Cash flow is usually strong because rent prices are decent, and the cost of the property is relatively low compared to places like California.

These areas offer strong appreciation potential, steady growth, and stability.

Everyone is transaction based.  

Yes, as S-Corp owners deferring salary into a Solo 401(k), you must still pay FICA taxes (Social Security & Medicare) on the deferred income since FICA is based on W-2 wages, not taxable income.