Very intersting topic..
I also agree that in the end it's difficult to express an opinion...I currently own 17 guitars ( including 1 low quality acoustitic that sounds pretty good) ,the only true vintage instruments I have are the Guilds I bought on e-bay in the last 3 years: 2 Hoboken ('64 T100D and '66CE100D) 3 Westerly ( 2 vintage '80s acoustics and a recent Blues 90) .
For many years I ,till the Ebay advent, I was just playing some good guitars I could afford in the absurdly overpriced italian market.
My mid-nineties Gibson Les Paul Standard '59 reissue was my main guitar for ages,it's great, sounds superb,has a gorgeous flamed top and everything, but I honestly have to say that the same London guy I bought it from for a bargain price had for sale also an almost identical ORVILLE Les Paul made in Japan with an even more beautiful top and that sounded much better than the Gibson...I bought that Gibson only because I thought that the future value and resale price would have been better.
I also own a 2005 Japanese Gretsch Tennessean with Hilotron single coils that is absolutely perfect,and to me is a lot more comfortable than the 2 1963 and 1964 Gretsch Country Gentleman that the bass player in my band owns and I often happen to play for fun.
But ,on the other hand, a 1966 original Tennessean that I played years ago was so stunning comfortable,beautiful and had the ultimate Gretsch tone that after playing it I was convinced to buy that model....
I love dearly my 2 Rickenbackers ,a fantastic 2005 360 that I bought new, and a used 1997 620, never played a vintage Rick to compare it to my new ones though..
The same I could say for my other guitars ,Epi Casino, Danelectro, wonderful Telecaster with texas special pickups...
The vintage '60s Guilds I have are anyway something special, they're both in cosmetical good shape but they neverthelless ooze that mojo..the way the finish had aged shows the beauty of the woods in a different way from modern guitars, the brazilian rosewood of the fretboards is beautiful, they feel like they already lived a life..and ,most importantly ..they sound superb, that T100d is supposed to be a cheaper Starfire but those cheap and almost unknown single coils are some of the best pickups I ever played for my taste. I admit that the Guilds are the only top quality VINTAGE guitars I can afford, and why vintage 60s guitars that good are so cheap ( I got them both for a lot less than $1000 each..) is still a mistery to me ...compared to the incredible prices reached by vintage Gibsons and Fenders..could it be that those Guilds prices are the ACTUAL NORMAL prices that a good vintage instrument should cost and the other brands are totally overvalued ,mostly because of hype,myths and other non-musical reasons ?
I guess it's no coincidence that all the 14 guitars I bought on Ebay came with no issues,no defects, all perfectly playable ( except for the slim neck of my D50) for me...vintage or new guitars I bought didn't hide bad surprises even if I was forced to buy them online,with no chance to play and judge them before....was I particularly lucky?... maybe, but I also think that this means the average quality and build construction and crafting is pretty good nowdays like it was for those fabled '60s instruments that,as pointed out by others and by some of my direct experiences too, sometimes are not totally up to what you might expect from their market value...