When I got my '66 J some 20 odd years ago I was gigging crazy and going through basses regularly. I finally decided I needed "real" vintage and see what it was all about. Nobody was more skeptical than me about their aura. So I went to my buddy, a licensed dealer, to shop. He had 5 '60's ('62, '64, (2) '66, '68) and 2 early '70's J's, all complete and straight. Most with some playwear, one was immaculate.
Got to play them all for 2+ hours through a killer Demeter/Bergantino double cab rig. That kind of comparison shopping with no pressure was a real treat. Learned a lot with this playthrough. Vintage does not equal automatic manna.
It was the peak of the "gotta get me a vintage" bubble and I paid a premium for this one. It's not a closet classic and clearly was played a lot, honest relicing. It plays beautifully and AFAIC it has enough of "it" to keep me satisfied. It still makes me smile whenever I play it.
So, I'm sure I'd never get all of my money back in a sale. But feeling that I found a good one makes its value established for me. I just feel pretty lucky to have it.
P.S. My first real bass was a brand new '70 Telecaster. Still got that too and its value is beyond measure.