To clariy - when I say 'realistically, this is a very small to medium amount of your annual budget' I was specifically meaning the difference between the two numbers ie 8,000. If you have the budget to eat around 28k or 36k the difference is likely not killing you. Of course, this math could be off as I pulled the end values of the boats pretty much out of thin air. But it has to be admitted it would be easier to sell the 10 year old cat than the by then 15 year old cat.
You could go the other route and try to source a throughly depreciated boat (say, 10 years old) that surveys impeccably due to low and conservative use.
In other words, assuming everything but the engines (maybe!) on a 1998-9 otherwise beautiful boat is in need of replacement, and argue the price down from there with the assumption that all the electronics, some of the wiring and some of the plumbing will be replaced and that the engines may require mid-life service.
We pay a great deal for style and the perception of style, but in some cases, the best or most logical design of a type has already been produced, particularly in a relatively conservative area of design as small yachts. There are many examples of 25 year old designs that have been merely tweaked or updated in terms of trim or electrics and still find an audience.
My point is that the middle distance of the used market holds more bargains than the "newly used" primarily on the basis of perception and the desire of the dealer to recoup the initial cost as much as possible, whereas a 10 year old boat owner knows that his boat (even if it has been only daysailed 20 times and maintained and serviced religiously by marina staff in that period) will labour under the impression of "old, out of fashion" and will be priced accordingly.
The next step, of course, is "classic", at which point the boat will hold or increase its value somewhat based on reputation and whether or not someone does a circ and writes a book praises some otherwise unremarkable 1988 cruiser...