Do you wish you had that car today?
Not really. '49 Chevs back then - 1965 - were typically all worn out at 10 years, 100k miles.
I had bought this cheap from a neighbor when the grinding noise in the transmission had become unbearably loud, and installed a $15 junkyard transmission to get it back in usable condition. I said above it was a $100 car, - just to simplify the post - but I'm not sure I had even that much into it.
At various times I did own cars I was certain would become classics. Most notably a $50 '36 Ford Coupe I bought even before I had a drivers license. Just an old car then, like today buying a Ford Pinto. But beautiful Art Deco styling. Searching today to illustrate this post with a photo, I see this one sold for $65,000.
Parents were outraged I had a car before a license, made me sell it.
Other notable cars I owned: Apparently a 1930's Dodge pickup as viewed from the rear, walked around front and discovered it was a 1930 Chrysler Imperial cut down with its vertical back spliced on perfectly just behind the seat then the Dodge pickup bed beyond that. But it had a minor rod knock and I couldn't afford to make it right, also I doubt it was suitable for freeway speed. Sold it.
My high school hotrod was a '37 Chev coupe with a Chev 265 (the first SBC). Terrorized the neighborhood with that. Then a relative offered me their '50 Olds, excellent condition, the same model CHP had used for their patrol cruisers. Fastest car sold in 1950. Sold the Chev and drove that for several years.
Many more classics. From an English Austin, BSA and AJS motorcycles, various Willys Wagons and Wagoneers, lots more including 2 Volvo PV544's.
Most cars were chosen out of a love for the classics. Cars don't rust in California so the condition of an old one, depends entirely on its maintenance history.
I'm still driving the 1999 Subaru Outback I bought new. It hasn't given me any reason to replace it.