wow I will see what I can remember
starting with my first car:
1983 ford ranger 4x4 5spd 2.6l V6 ... $300 .. drove it for years, was very mean to it, it held up very well and I sold it for $500
198* oldsmobile delta 88 .. auto.. 320 V8 .. free .. giant land yacht, put a holley 4 barrel racing carb on for tire squealing fun times
198* buick POS.. no amount of repairs would stop if from overheating.. yet I commuted with it for a while
1991 pontiac sunbird 5spd 2.1l 4cyl... nice new car but what a POS as far as quality
198* chevy pickup, diesel
198* ford f150 custom 451 windsor v8, column shift manual, good times, good offroad for a 2x4
1972 chevy c10 I restored to classic good condition, bored out a 454 V8, racing carb/cam/etc, posi rear, etc., big fun pickup truck that could do wheelies
1989 jeep cherokee 4x4 v8 with big fat mud tires.. unstopabble offroad until the transmission ate itself in the forest and I had to drive out 4 hours through the swamp in reverse
2002 kia rio wagon thing.. cheap new car, very very gutless engine
-1982 yamaha xj650 maxim motorcycle.. was a sport bike it it's day and it shows, 180 km/h no problem

-still have it, ride it to work every day
-2007 honda ruckus 50cc scooter! still have it and ride it sometimes! it is kind of offroad capable
-1992 mitsubishi delica, the ultimate camping/exploring/fun vehicle!

-weekend / grocery / offroad / heavy rains vechicle
what next? I really want to have a city car and a non-city vehicle. I'm kinda poor though so I'll probably end up with something fuel efficient for the city and something like a $2000 zuki samuri or geo tracker for out of the city. Would be really tough to get rid of the delica though I really like it :)