IMO this whole issue of new (newish) vs. old (older) at an equivalent price
point (has to be, otherwise the comparison is not valid) is repeated over and over again in all other major buys a person makes. Is the brand new house better than a well restored 19 century Victorian? Is the new entry Corolla better than a 20-30 year old, then top of the line, Mercedes? Is new "made in 3rd world" suit from a discount chain better than a 5-10 year old top quality tailor made suit?
Of course it's easy to see that a brand new quality item is better than a 30 year old same quality item. But this is not proper choice as people who can afford new good stuff don't need to compare it with new so-so quality item or old good quality one. Myself given a choice of entry level or smaller sized new/newish boat and a larger older one for similar $$ I will always chose the older one as I am, having observed general deterioration of quality over my lifetime in practically everything that is mass marketed, not very keen on the new stuff in general. This is not new but has been going on for about 200 years when mass production and mass marketing
replaced craft and small artisan based economy. The quality maker's and worker's wages are just too prohibitive for a mass production run so they have to rely on either low skill worker in a conveyor belt like production or dilute the quality of the materials or both (most likely). So by definition, everything else being equal
the new anything is not built as well or by as well trained worker as the similar item built generations ago. Yes, technology is a factor but only where it is really needed or is the very reason of the item such as TVs, PCs, phones, etc. But even there older TVs, telephones or fridges would function well for dozens of years whereas new generation become obsolete or start malfunctioning in less than 5-6 years. MY old fridge lasted over 30 years and not a bin cracked or glass broken. The new one is less than 4 years old and already all bins are cracked or chipped and one glass shelf cracked and had to be replaced.
But a sailboat being nothing more than a tricked out piece of fiberglass
hull can be easily updated by installing items which even on a newish boat have to be updated every 10 or so years - rigging
, etc. Other than aesthetics I just don't see the point, given a similar price range
, to choose a newish smaller/lesser quality builder
boat over an older larger well maintained better known brand name one. And my personal dislike for the plumb military ship style bows doesn't help either.