Yikes!
You guys sure get around!
This will probably the shortest list here then for someone my age:

1968 Datsun 510 wagon (used, $600 in Jul 1976, while still university student).

1978 Subaru 4x4 wagon (new, $7800 in Jan 1979, right after starting work).

1987 Dodge Raider (new, $16,900 in Aug 1987, needed the extra power to tow a boat trailer)

And that's the whole list.
Still driving the Raider (=Mitsu Montero = Mitsu Pajero), just passed 400,000km.

Don `87 Mitsu 2dr, Rubicon survivor, GModified.