What would be better to ride today ?
A top of the range 20 year old board with a matching top of the range new rig ,
or,
A top of the range 20 year old rig with a matching top of the range new board ?
The old stuff being in new condition.
I understand there will be servere mismatching .
If there is a definitive answer , will it be on all disciplines .?

Easy for me to choose. Mainly doing blasting around bump and jump conditions a solid older board with more narrow outline and new sails. Wouldn't want to go back to older sails

I think sails have progressed more in the last 20years than boards.
Although to the casual eye board appearance has changed more, getting shorter and wider.

But getting tip twist sorted in sails has improved, their performance no end. on an old board the mast track may be too far forward to take real advantage of this, but I think it would feel better than an old tight leach sail on a new board.

I have a couple of boards that are close to 20 years old, that I bought used, and they are still fun. I've seen some older sails and the designs are so different with completely different shape that they look like the feel would be totally different.

I see an old North sail that Ezzy designed before he moved to his own company and it's a tall single cam design with strange leech shape and it seems like it would handle so differently.

I'll take the new rig any day.

Those old sails quite often have a nice "sweet spot" but little range. Had more grunt but also more drag.

Have found the durability of sails decreases a lot with consistent use, even full x-ply sails, so finding a good 15-20 year old sail that can stay together might be a challenge! Imo different for a board as materials appear to have a longer life span if looked after reasonably well. Performance wise agree with others that sails have come a long way whereas boards haven't altered as much, with some newer non-wide-style boards still available. Still using a 16 year old jp fsw board that has had a few repairs but puts a big smile on my dial whenever I use it!

Can't comment re all disciplines as only sail freeride & speed gear.

Old board n New sail for me.
Old boards are tougher n do it just as good, albeit differently.
Mostly about how they get on the plane.

I liked the way the older longer boards got on the plane quicker, but on the same token I like the way the newer boards (around 230) fit better inside a station wagon. I'm also not convinced that shorter wider boards plane faster as advertised, but that's just my opinion. I like heavier older boards.