My dad had one of everything, but concentrated on Corvettes.
He started with a Model A, then a 39 Mercury I think. Drove a TR3 through college as it completely rotted away around him. When I was shopping for a LBC in the late '80s the only thing he told me NOT to buy was a TR3.
In the late 50s he couldn't settle on what he wanted, but could only have one car, so he switched back and forth a few times. Austin-Healey 100-4, then a 59 Corvette, then a 100-6, then a 60 Corvette, then a 3000, then a 62 Corvette all in fairly rapid fashion. He'd get the Vettes from used car lots that didn't allow test-drives on Vettes so the rides home in those were always adventures. He looped one of them dropping the clutch leaving the parking lot.
When I came along he had a 64 1/2 Mustang and a Tiger. He wanted the Tiger to be faster so he yanked the 289 out of the Stang and, after a surprising amount of work, dropped it into the Tiger, and stuck the 260 in the Mustang, and neither car worked particularly well after that.
He did ice racing, ice trials, gymkhana, solo 1, everything with whatever he had at the time. He also did road racing in a pair of Spitfires (GP and FP), towing the first one with a 67 Vette 427/435 4spd convertible. He had a Karmann Ghia briefly and sold it, then borrowed it back to go ice racing, and rolled it over.
In the late 70s/early 80s he because known as the neighborhood Honda guy since buying a new Civic in 1974. People would tell him about a dead Honda somewhere and he'd pick it up for nothing. He had cut holes in the garage roof so he could drop chains from the joists and pull the engine with a block & tackle. He could rebuild the engine over a weekend and have a running car in a few days. Some of those Hondas were sold at a tidy profit, some were turned into ice race cars, and some were issued to us kids as we got to driving age. I went through four of those myself.
He liked having projects, and bought a handful of non-runners, abandoned restorations, stuff like that and for the most part wound up with decent running cars. One was an early Buick Riviera that just needed the interior done. He finished that, drove it for a few months and decided he didn't like it. A more serious one was a 100-6 that had all the metal work done but was completely unassembled. He said it was like a Cobra kit without the instruction manual. He got it put together, drove it for a few months and decided he didn't like it. On the plus side, he made money on these (assuming he worked for free). He also built a Factory Five Cobra on the cheap: no chrome, no go-fast bits, one single donor car and his own paint. He really liked that one and kept it for twelve years or so before selling it. I drove it once and wondered how he could get his 75 year old frame into it because it was completely uncomfortable for me.
He sold that 67 Vette and replaced it with a 62 in the middle 70s, and still has the 62. He told me that it was going to be my inheritance when I was 10-12 years old, and to this day it has been the only car he's owned since I got my license that he hasn't let me drive. I haven't asked.
When I was graduating high school (1985), he had three Vettes: the 62, a 71 454/4spd coupe, and a 73 convertible he picked up cheap because it needed work. He got the 73 running and driving, and when I graduated he let me use that for the summer. Nothing like setting a 17 year old into the world with a screaming yellow Vette convertible to learn manual transmission on.
Recently he had a small fun fleet: the 62, a yellow 04 Vette convertible, and a 16 GTI for rainy days. He didn't really like the C5 and sold it, thinking of getting a new Vette. When he saw that the C8 was going to be automatic-only and not a real convertible, he swore that off. He wound up placing an order for a C7 on the last day dealers were taking orders, and over the summer he took delivery of a red/red '19 7spd convertible. I saw it over Thanksgiving but the only involvement I had with it was helping him put the cover on it so it wouldn't get dirty in the garage over the winter. I hope I am still having that much fun with cars when I'm 85.
He had some other fun stuff in addition to the above: 914-6, Datsun Roadster, X1/9, a pair of MGBs, a pair of ice racing Corvairs, Saab 96 that was supposed to be an ice racer but he decided it was too good for that fate, a couple other early Mustangs... I'm forgetting a bunch I'm sure.
Random pics