I think I'm getting too old to remember them all. but a sampling would be...
1st car: 1959 Chevy Impala - fire engine red, 283ci a 3-speed manual with a non-synchro first gear
1st (and slowest) truck: 1962 VW microbus (only 36 horsepower, but valiantly made it to the top of Pike's Peak)
Model year with most vehicles: 1965 -- Ford Mustang, Buick Riviera, Plymouth Sport Fury, Dodge window van, Ford F100 pickup
Biggest car: 1969 Chevy Caprice station wagon (could lay down a 4x8' sheet of plywood and shut the tailgate with room to spare)
Most number of Toyotas in the driveway (with my name on the title) at one time: 2013 Prius v5 wagon, 2008 4Runner Sport, 2010 CamryXLE, 2002 MR2 Spyder
Contrasting vehicle reliability: 2002 4Runner vice 1971 Fiat 124 Spyder
Last car purchased - the Prius, and last truck purchased - the 2000 LX470
And
@re_guderian - 4 mini-vans: a Dodge Grand Caravan, a Plymouth Caravan, A Ford Windstar, and a Mercury Villager. There was also a Dodge Colt Vista wagon, not sure if that counts for a 5th or not.