In order (left out a couple; sometimes owned 2 or 3 of these at once):
1984 Pontiac Acadian
1985 Chevrolet Chevette
1987 Chevrolet Spectrum (Super lame car. My dad talked me out of a Firebird and into this... I sold it after 6 long weeks)
1985 Bronco II
1987 Nissan Truck (this was cool - roll bar, lift kit, big tires, nice stereo, etc. and I was only 17)
1978 3-series BMW (mint!)
1984 Bronco II
1987 Celica GT-S (fun car)
1991 GMC Sierra (step side, looked a lot like BC Chris' truck. That was a fun vehicle)
1993 Ford Explorer (pretty nice SUV. Drove it to Newfoundland while sleeping in the back the whole way there and back.)
1991 VW Passat wagon. (red, 5-speed, loved this thing. My wife and I still rate the highway driving characteristics of every car as better or worse than the 91 Passat. Have not found a better one yet.)
1995 GTI. (boring and lame. I'm finally willing to give GTIs another shot after swearing them off for 15 years. Will probably get one within the next few years)
1988 F-350 crew cab long box. (Bought this to carry our dirt bikes around in. Was funny having such a ridiculously huge truck/beater. Only vehicle I've ever had that I didn't baby. It was fun having a whatever vehicle for a while.)
1997 Ford Ranger (jacked up with 33" tires and lift kit. Did a lot of offroading in this. Great truck)
1999 Maxima. (boring car, didn't keep it long)
2000 Nissan Frontier crew cab (too gutless to keep)
1987 Mustang GT (bought it in 2005 with about 10,000 kms on it. It still had factory transportation plastic on the back seats that I had to take off. Modded the crap out of that car. It was fast and crazy)
1997 Ford Expedition. (really liked this one. Super comfy)
2007 Sienna (great vehicle)
2005 Chrysler 300c AWD. (favourite all time vehicle I have ever owned and I kept this longer than any other vehicle too.)
2008 Toyota Tacoma (work truck. It was nice)
2011 Jeep Wrangler 4-door (kept this thing for about 3 days and returned it because I hated it so much. Gutless God awful vehicle)
2009 Pathfinder. (last nissan I'll ever own. I hate them)
2005 Mustang GT Convertible (just sold this a couple months ago. Had a lot of fun in it and really liked it but just wasn't using it enough)
Current Fleet
2011 Toyota Sienna XLE (best people mover ever)
2014 VW Passat TSI (haven't APR tuned it yet, but think about it daily. Hoping to find someone who has tuned the new VW 1.8 turbos to give me a firsthand green light... Anybody?)
2012 F-150 (work truck; really like it)
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