It is important to differentiate between the Cape Dory 25 and 25D. This comes up a lot, but they are two completely different boats.
The 25 was originally produced by Allied as the Greenwich 24, designed by George Stadel. It is lighter, has an outboard well, and less interior space/headroom. The 25 was produced for about 10 years by Cape Dory.
The 25D is an Alberg design with an inboard diesel and substantially more head room. The production run was smaller and these boats are harder to find, in addition to being more expensive. The 25D has made fairly substantial passages and John Vigor discusses it in one of his books.
My general recommendation for people desiring a 25D is to look at other CD models, unless they are absolutely set on the 25D. They are one of the best CD designs and it has the most functional interior of the smaller Cape Dory boats, but they are harder to find and generally much more expensive. You could likely find a 27 or 28 that is heavier and has a little more room for less money. The combined production run of the other boats will likely make it easier to find a boat as well.
Also worth noting is that newer CD models (1980+) tend to demand a higher premium than 70's models. While the build quality of structural components (hull, decks, etc) remained consistent until shortly before their downfall, the interior trimmings on some models were not as good in earlier boats. The general layout will be the same, but later model boats may have a few extra racks, shelves, and better quality wood throughout. If that doesn't matter to you, finding a model from the late 70's will save you some $$ for other improvements.
As for the 25, there were a lot built and you should be able to find one easily, if that's what you want. Do not confuse the two boats, though. The 25 is well made (I'd shoot for later years, though) and owners seem to like them, so this isn't a knock against them either. They just don't have the same qualities that a number of the other Cape Dory boats do.
As for not pointing well, I don't have that problem (CD27). Sure other boats point closer, but we're talking a small margin. I'd take the quality and construction of the CD over being able to point a little closer any day. They also have positive qualities that a higher pointing boat may not have. Like anything, it's a trade off.
There are some gotchas with all the Cape Dory models, like with any boat. Most problems or issues are not uncommon to fiberglass boats in general. The most common and talked about problem are the chainplate backings. Earlier model boats used mild steel backing plates for the chainplates, which isn't a problem unless a leak occurs in the thru bolts. I've seen some that have no rust at all and others that flake apart, ours are somewhere in between. They also aren't easy to inspect (I use a $25 borescope to inspect them) or replace. Some owners have replaced them with stainless, some have gone external, and others don't have any problems. The later model boats used aluminum which AFAIK
has held up better.