My wife's 1998 Ford Expedition Eddie Bauer.

It had 185,000 miles on it and still ran great. We put over a 100K on it ourselves and it was great for hauling kids and other crap around town. For some reason we decided that it was time to replace it so we got an 05 Z71 Tahoe.

This is the vehicle I regret selling second most. We replaced that with a BMW 325i for better gas mileage and didn't see any sense in having two gas sucking SUV's. (Tahoe and 4Runner)

This plan has now backfired on me because my wife is wearing me out about the BMW being too small to drag small kids around in. I can't really argue with that because compared to driving big SUV's, the BMW is tiny. I've tried to swap with her but she hates my 4runner. Crazy woman!
So now I'm in a situation where I may have to sell the 4Runner, drive the BMW, and get here another Tahoe. I guess there are worse fates than having to drive a BMW 5spd back and forth to work but I really don't want to get rid of the 4Runner.
Long story short, my vehicle sale regrets might cost me 4Runner which I had planned on keeping for many years.
(Stock google photos but exact representations)