1990ish Honda CRX - First experience with a go kart and it was great. Got up to 110 and it was fun, but never again (too old now)
2002 - Honda Civic EX. Had like 11 people in at once in High School. Reliable car that held its value
2008 - First BMW - a 2008 528i BMW!! The Civic lost like 4K in value (wish it was the same for the BMW)
2006 - Z4 Coupe (one of my favorite BMWs and it is owned in unison with the 528i)
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