Gas Vs. Deisel (are we crazy?)
There''s nothing wrong with inboard gas engines for your intended purposes but if you are buying a 25 footer with "all the accomadations we could acquire" then I would say that an outboard is out of the question for your intended cruising grounds.
To explain, A properly maintained inboard gasoline engine, while slightly more dangerous than a marine diesel,is still a pretty safe and reliable engine. In my lifetime, with one exception, every boat that I have ever heard of that has blown up or burned, has had a diesel, and usually propane. In sailing, people tend to be pretty selective about what they fear. These days people have a deathly fear of gasoline inboards but think nothing of carrying propane, a far more explosive material, in boats that lack the ''explosion proofing'' of a boat with a gas engine. The electrical systems on marine diesels are sealed so that they do not produce sparks and the carberators have backfire supressors so that the risk of a gas engine ingiting itself is fairly minimal. Gasoline boats have bilge blowers that are also sealed units which vacate any fumes in the bilge. Using reasonable precautions, running the bilge blower and sniffing the bilge, the risk of explosion is minimal. You can then probably buy a nice 27 footer with an atomic 4 in your price range and do very well for yourself. (There''s a huge difference between a 25 and 27 footer for what you are proposing)
Outboards are a pain in the neck for the kinds of thing that you are proposing. In the kind of short chop sometimes with no wind that you are dealing with in these venues, they are really exposed to getting dunked and then airborn, eventually leabing you with no wind and no engine. Some people recommend outboards in a well. In my experience these are the worst of all worlds.
There are a lot of good boats that should meet your needs (To name a few):
Albin Vega: You can often find one of these with a diesel for less than your budget.
Beneteau First 28: While Beneteaus take a bit of a hit in this country, the Frers designed 28 was a pretty nicely designed and built little boat.
Bristol 27: Nice boats in a lot of ways. I have spent a lot of time on these. I like the mid-1960''s model better than the later ones.
Cal 27 or Cal 27-2 (Cal 2-27)
Ericson 27: You''ll need to try to find a clean one but these can often be found with a small diesel in your price range.
Hunter 27 (Late 1070''s early 1980''s) While Hunters, like Beneteaus, take a lot of verbal abuse in this country, the 27 was a pretty nicely designed and built little boat. That said you need to find one that was maintained pretty well as these boats were sold cheaply and often allowed to go to pot.
Oday 27: While pretty low on this list you can find these very cheaply with inboards.
Oday 28: (try to find one before they went to a sail drive)Good little boats. I like the fin keel versions better than the K/CB.
Pearson Triton: (Although the 28 is probably a better boat for what you want to do)
Soverel 28: These were really built for exactly what you want to do. Last time I looked there was one on Yachtworld with a diesel for $9500.
Tartan 27: This would be the Bee''s knees for what you have in mind. Whiel not all that fast, these are really good all around boats.
The point here is that you should be able to find a perfectly suitable boat within your price range, some with diesels, some with gas inboards. While smaller, older boats take more skills to sail in the places that you are considering, and certainly these older boats require a lot more maintenance skills and costs, they can be just as satisfying to own adn would be less expensive to own than much the much bigger boats that are the norm.