Hmm...
1981 Oldsmobile Omega (parent's leftover / college car) Manual transmission, manual door locks, manual crank windows, no power steering, no AC, AM radio only. Pretty odd stripped down Oldsmobile, but it was actually a really good car because there wasn't much that could go wrong with it. Was a monster in the snow too.
1986 Pontiac Sunbird Turbo (purchased used) (The turbo blew under warranty, the dealer botched the repair and had to replace the entire engine...)
1989 Honda Civic (This was a GREAT car and what I should have gone with as my first car. I liked it better than the 2000 Accord.)
1995 Mitsubishi Montero (I actually liked this quite a bit, but there was less than 0 aftermarket support for it)
1995 Land Rover Discovery (purchased used in 1997) (Had a lot of fun with this, but the quality control was the pits...)
2000 Honda Accord (Bought as the daily driver after lifting the Disco. Like the Civic, this was nice, but I thought the older Civic was better built)
2005 Nissan Pathfinder (Replaced the Disco and Accord, but was very cheaply made)
2006 Lexus LX-470 (Loved it, but traded it in when gas prices spiked and I had a long commute at the time)
2008 Toyota Highlander (No complaints)
2014 Range Rover (I was debating about this and a G550, but went with this thinking it would be easier for my elderly mom to get in and out. What a POS, but they were in super high demand at the time; I pretty much broke even trading it in after 6 months.)
2014 Mercedes G550
2016 Mercedes G550
2017 Mercedes G63
2020 Toyota Land Cruiser HE
The Mercedes G’s were all a ton of fun. I traded the first in for the engine and infotainment updates in the 2016 and traded the 2016 in because I wanted the much nicer seats that were only available in the AMG models and wanted to do so before the major redesign as I knew I wouldn’t want the first few model years (or so) of that. The MSRP went through the roof on the redesign, so my next vehicle wasn’t going to be a G. After some parts availability issues and concerns over long term service costs and reliability, I decided to get the LC. Now that the LC seems to have been cancelled in the US after 2021, I’m glad I made the move when I did as I hate the front bumper design on the current LX.
I‘m hoping to finally settle down and keep the LC for a long time, but history suggests I’m not good at that... Very happy with it so far.