A lot less detail, but my process was very similar. Only difference was I did it with both cars and trucks at the same time. Over about 10 years....
MazdaSpeed 3 -- Fun car, but it had some insane rattles that I could not abide. Sold it and bought:
STI hatch -- loved it, but was commuting 300 miles/week and the poor mileage drove me crazy. Sold it (for what I paid for it!) and bought
Subaru Impreza. I'd had my fast hatches. Now was time to settle down. This car handled my needs just fine, for about a year, until i started going to the track. Sold it and bought
Subaru BRZ. What a great little car. Perfect on the track. Spent $10K modifying the suspension, wheels, brakes, supercharged it, all to drop 6 seconds off my time. Got divorced, and this wasn't a good car to go out on dates. Sold it and bought:
BMW 428i. Seemed more mature. Still pretty fun to drive. Not "fast" but "fast enough". When the lease was up, I was ready for something sporty again.
Corvette GrandSport. Not the fast Corvette, but I have no regrets. NA, MT, I think it looks great, and anything more would feel like overkill as a daily driver. I've always wanted a Corvette and the C7 is a great combination of decent interior, nice exterior, great performance, and pretty darn good highway mileage.
Meanwhile, in the other half of the garage...
Ford F-350. We lived in the boonies, were building a lot of retaining walls and hauling tons (literally) of gravel. This was a great truck, but then the recession hit and GM started giving away trucks. Couldn't turn down 40% off MSRP for:
Chevy 2500. Felt much more refined. But I didn't like it. Not sure why. Didn't handle nearly as well off-road as the F-350. Most of the property work was done, recession was over and resale values had gone back up, so sold it for a smaller truck
Chevy 1500. Bought at a firesale price after rebates. Drove for a year. Not a fun truck, didn't manage well off-road. Meanwhile I spent a lot of time in Death Valley and really wanted to go back with a more capable vehicle. Traded in the Chevy on a
Ford Raptor. Horrible mileage. Otherwise I loved this thing. Drove great on the road and let's just say it saw triple-digit speeds off-road in Death Valley. Beat the hell out of it, but the shorty bed couldn't even fit a bike in the back, much less a full-size ATV. Payload was like 700 pounds. Resale values were insanely good, so I made a profit selling it after 2 years and 20,000 miles. Bought
Ford F-250. Building a new house, hauling lots of supplies again. Started renting from Home Depot, but quickly tired of that so time for another truck with decent payload. Then I got divorced, had to do a lot of moving stuff from house to ex-'s new house, house to storage unit, and wanted to to do some camping with my bikes. Sold the truck and bought
Ford Transit. Fun van. Amazing how much you can fit in there. Even with two rows, I could easily sleep in the back with supplies, road bike, mountain bike, fridge, etc.. Used the heck out of it for a couple years, but it couldn't handle snow at all. Sold it and bought
Ford F-150. I've still got it for now. Not my dream truck but it's been OK. I'm 50% confident that a Bronco is in my future once the initial MSRP+ insanity is over.