Counting cars and trucks (if I remembered them all) I've had 50 including my wife and son's while he lived with us (that I bought and insured). Son had two of them, so 48 if not. Bikes (same, ones I bought and insured, 2 were son's while living at home) total 19 street bikes. Have been at least 10 dirt bikes also. Plus Slingshot.
Counting the SS, all cars that I was the main user, all bikes that I was the owner/rider.... I've had 58. That's one for each year of my life. Need to be looking for the next one, no reason to wait until I turn 59!