All good points made above. For myself I had a background with long race boards and loved the way the things railed up and pointed. When teamed with a quality rig (of the time) then in stronger winds I would be all over the top of the run of the mill slalom boards. Also I had a DSB and remember some good times and iffy gybes.
That said, there were some very ordinary long boards out there and the average rigs were well, very average. A couple of seasons ago I had a try on a 'nth' hand long board a friend had bought. Pretty ratty condition all round. I could not sail the darn thing it was so bad. That is the kind of gear that should be taken away and minced.
Sure there will be older hardly used gear. But even then I see so many returning WS people buy such and a month later have moved onto (second hand) modern gear and are progressing happily.
Among more experienced WS I see some moving down to smaller volume boards and more hi tech sails and after a bit moving back up in volume and down in rig complexity as they seek their comfort level. The point being there is a happy medium for everyone - each to their own! There are certainly some good 'plug and play' boards out there and I have experienced the humiliation of being blown into the weeds by such when on my steep learning curve required of some 'specialist' gear. But the payback is there.