It's all about refined local knowledge, choosing the right location and building type, and good timing always helps (but shouldn't be the primary driver of your success.)

So he got $30K from the insurance (his attorney got 1/2) and then he settled for an additional $10K from the defendant (driver). 

I remember they use to have a policy when I was first licensed over a decade ago that if you didn't personally know the buyer then have them come in to the office first.The office then took pictures of drivers license and info etc. of the buyers.

Happy you are back in the driver's seat and you were able to get your life back and make your most important partner happy, your wife. 

I own an older model sedan I use as a daily driver, and for purposes of my rentals they always see me in that car.

Remember, opening escrow puts you in the drivers seat to negotiate. 

I am a truck driver and Custom T-Shirt Printer.

I expect to collect on that policy at some point though because I'm an awful driver and am in lots of accidents.

Had they said, "Before you buy this car, please know that if you are rear ended, the gas tank may explode and spew gasoline all the way to the drivers seat, before engulfing your family in flames, and we want you to know that we can fix this for $11," I'm sure most people would have said let me pay for the $11 upgrade.

I don't know your market at all but based on your profile goals and background I don't see the driver for leaving your market.