Believe it or not, there aren't too many resources stressing the differences between vintage and modern saxophone mouthpieces. What makes an old Otto Link from the 1950s justify a $500-1000 price tag? Why are the new ones only $200-250?
Is there a tonal advantage to playing through a really old one? I would think the opposite, as modern technology would make modern mouthpieces more consistent.
So, just because it's old or expensive, doesn't mean it's good. I've played quite a few old links that are horrible. And I've played some that are incredible.
Old Otto Links are tricky because they are pretty inconsistent. Finding a really good one that fits your playing style takes a lot of trial and error.
The reason why they are expensive though is more than just collector's value. Despite their inconsistency, you are guaranteed to find a good one eventually. So their value is due to the fact that it is a reliable option. If you find a good one, it will be really good. And then to you it will be worth the price.
My favorite was a modern link that had been refaced. I found it randomly one day in a little music shop in LA. I've yet to find anything that plays as well as it does. My sax got stollen a few years ago along with the mouthpiece, and honestly the mouthpiece was a bigger loss than the sax. It was a Yamaha 82Z. You can find a million of those that all play the same. The mouthpiece was one of a kind, and the only one I played on for about 10 years. So it was a much bigger loss.
One interesting thing about that refaced link is that while the tone was incredible, playing overtones on it was really hard. Something about the shape of it just made it tricky to hit them. Overtones were never a big part of my playing, so it was fine. The lower altissimo was easier than overtones, but still difficult. I had a backup modern metal mouthpiece designed specifically for overtones and cutting through that I would keep in my bag just in case I needed it.
There's quite a few mouthpiece makers today that claim to be vintage link clones. To me, none of them sound like vintage links. I feel like it's more of a marketing gimmick. They are completely different.
Honestly, it's the combination of being a collector's item, and they were made very well, and it's quite likely that it's been refaced by a master refacer at that price which is worth a lot too. If you don't care about the collector's item part, you can get just as good a mouthpiece from a modern link copy, but if you want it just as good, expect to pay what is still serious dough ($400-1000 probably). Modern copies that I would put in the same category of quality include Theo Wanne, Aaron Drake, Navarre, Ted Klum, and Mouthpiece Cafe, among others. Very small physical differences make a big playing difference in mouthpieces, to the point that the skill of the finisher is significant. When you find the right high end mouthpiece for your horn and embouchure, you won't believe how well it plays and $500-1000 is totally worth it.
This is a difficult question to answer in a non-subjective way. What I will say is that there is a bit of a legend among saxophone players that old saxophone mouthpieces were made with materials (perhaps toxic materials...) that are not able to be manufactured today, and that these materials simply sound better. Some of the mouthpieces are physically rare as well.
