My 1st guitar was a 64' Jaguar bought in 1987 from a flea market for $300-$400! My parents bought it as a grammar school grad present. That thing was like a "new old stock" condition. I'd kill to have it today. It was mint. Nice sunburst that literally looked like it was bought, looked at, and kept in it's case for 23yrs.
I took lessons with it in and my stupid butt traded it in on a Custom Strat in 89'. Obviously now I could kill myself for having parted with it but at the time Strats were it and I had never had one of course. I never considered the investment (being 15-16yo) and I didn't know it would regain a huge popularity 3 years later.
I had 2 other chances to buy 2 different vintage Jags in early 91' at a local vintage instrument shop... both 65's, both Sunburst, one with a bound neck. Both were under $800, one was in great condition and the other basically mint aside from heavy strumming wear... the body itself was perfect, hardware like new. It would easily go for $3500 today.
Now I'd love to have a vintage but I can't bring myself to pay $3000 for something I passed up for $700 or so. It's like a nightmare knowing I could've had that one from 87' which I think could've fetched $4k today. Not a rare color, obviously, but it was like NOS even after I used it for two years.
My Jap 62' reissue was around $400 back in 96'.