I think this really breaks down into two distinct questions - 1) Would a single vintage guitar be a better financial investment than a wall of regular guitars? and 2) Would a single vintage guitar be better for someone who plays a lot of guitar?.
On the first one, it is certainly possible that a single vintage guitar could end up making better financial sense. There are plenty of high end collectables which do retain their value over time, or even accumulate value, depending on how collectable they are. Stradivarius violins are an obvious parallel, but also classic cars and rare firearms and so on all have similar profiles. If something is "a classic" when you buy it, it will probably still be if/when you sell it.
On the second one though, absolutely not. The only way that a vintage guitar retains its value is, basically, by never leaving its case. It may have perfect tone, it may have the most beautiful finish, it may have been personally licked by Jimmy Page, but if you bonk the headstock against a wall you can almost hear your wallet screaming in pain. No matter how careful you are, you are still putting more mileage on the clock.
And that's the real problem - These things cost so much that you (or me anyway) can't justify spending that kind of money unless you know you will get it back later. But the only way to make sure you keep the value is to not play it.
If you are thinking to sell a bunch of collectable guitars and get one uber-collectable guitar, while also having your daily beater guitars to actually play - Yeah, that could make sense. But liquidating everything just to have one uber-collectable guitar? Nah, you'll end up buying more guitars because you don't want to play the one really expensive one.