63, I get where you're coming from, but part of your criteria is playability. I've played a few old ones in friends collections. Particularly older strats (I never got Teles). Some of the 80s ibbys I get and the collector in me really wants some of those 70s Ibby LP copies(what is it with guys and collecting things, I suspect if many of us were laying in bed with the most beautiful woman on the planet we would secretly think "wow if only she had a twin sister").
What I tell people is have new guitars, or recently used ones be the ones you practice and gig with and save the vintage axe for recording. There may be a better tone to an original 1980's RG when it's recorded, or it may just be the same thing as today's RG but old.
You have to determine if a true vintage guitar, like a coveted 80's RG, Jem or Gibson/Fender, is worth spending the extra money for and if you only go out on a branch and get one such vintage guitar, it's no great loss. It would be terrible to buy a whole bunch of vintage guitars, at great cost, looking for the perfect one only to find you really only like new guitars. There are quite a few guitarists who like stuff brand spanking new, relish in being the original owner, and don't like the used feel of an older instrument. That's OK too and it's what makes us all different.
I may not claim older guitars were way better, but it's hard not to like a 20 or 30 year old pickup. I don't know if the harder edges get softened over time but there's nothing in the humbucker realm I have liked for (at least cleans) as much as my original early-60's Gibson PAF. People pay thousands for them and for a solidbody guitar, most of the sound is attributed to the pickup. Pots, wiring, switches, wood choice, neck choice, and fingerboard choice all play a factor but for a solid bunch of wood with some metal and plastic, the pickups end up being the overall voice of a Les Paul, strat, or RG. If a person doesn't want to go out and get let's say a rare vintage Ibanez, you can always buy a vintage Ibanez pickup like Super 58s, 70s, or 80s and sometimes radically change the sound of a new guitar. It's the cheapest way, at this time, to get the old, vintage sound. There may come a time when there's a pitch perfect digital effects box/software that can get the sound, but for now, eBay and old Ibby pickups can get one a big part of that golden era of Ibanez sound. Same goes for old Fender and Gibson pickups, too when it comes to solidbodies.
So if somebody says it's the maple, mahogany, or dedicated workers in the past that makes a vintage guitar different, they still won't play as much a part soundwise as the aged pickups. Short of spending sometimes too much on some genuine vintage pickups, you can get some Seymour Duncan aged magnet pickups which get that basic vintage sound people chase after. It's a real sound and while not radically different than the sound of a similar new pickup, there are those willing to pay extra for that yesteryear sound.
You can also get a standard new tube amp that doesn't have too many bells and whistles and get some vintage speakers and see how you like the tone. Many of us who were used to gradually harder and harder rock upped our Marshall speakers or Fender speakers and got stuff with more kick. At the height of the modding years, many put EVs into the Fenders to replace standard Jensens. Also some liked hotter speakers than the Celestions for Marshalls and even Celestion made hotter replacement speakers to get a more biting tone. Sometimes too much power is harsh and I found that under a Marshall when I went with four 100 watt Jackson speakers. It was just too much and I had wished for four 30 watt Celestions. Louder is not always better and that's where old speakers and old guitar pickups come into play the most.
It's probably a fallacy to say they were categorically better in the old days, but that maybe they have a tone that people like which they may find hard to sort out under all the uber modern gear. I put in tens of thousands into old gear and maybe I shouldn't have but it was fun still looking for it everywhere and beating other collectors to the punch.