The Right Boat

Interesting background, you've come to the right place! Can't say I'll have all the answers for you, but here's a few thoughts to start the convo:

- Most 1990s gradys will have some degree of susceptibility to wood rot, especially at the transom. This can be somewhat reduced by targeting those with a bracket-style transom...
- ... UNLESS you buy one where the transom has already been replaced. You may have to go pre-1990s to find that within budget however...
-... which raises the hull design issue. Depending on model, most pre- ~1992ish GWs had a relatively antiquated running surface design that is less preferred by most to the SeaVee2 design that is still in use today. This may or may not be of significant concern based on your expectations for rough water ride.
- The camping angle obviously tilts the discussion towards walkarounds

Collectively this makes me think something like an early 90s 228 Seafarer could be a fit IF you can find one on budget.

There is a lot of info on the board. Prob best to do a search. Do older GWs have their issue - yes. Mostly due to wood cores but any 25 year old hull will have their issues.
The biggest thing is to make sure they are issues you can address or have someone do it reasonably. If not much experience a survey is a consideration.
There is no perfect boat. All are compromises tailored to a certain set of needs and use cases. If you can being in Maine, I'd see if a small cuddy can be had or something that has some cover from the wind and weather. Before you start looking, determine your use case and weather/seas you expect to be in regularly. Good luck. Overall GWs are solid boats if the weak spots are managed/taken care of and maintained properly.

I read through most of your post and think you're going to have to either change your budget a bit and/or the year of boats you want, as the pre - 1997 Grady White boats just had standard marine grade plywood and they can definitely rot. The 1997 and later models have a product called Greenwood XL and it's supposed to be much better at resisting rot, though some obviously still do. I think the other thing you should really consider is what kind of boat style do you want? Are you wanting a walkaround boat, a center console, dual console, etc? Grady White makes dozens of different years/models of boats in that 18-22' range and think that you should definitely narrow your search down a bit by trying to figure out what style of boat you want. For example, I have a 228 Seafarer which is a walkaround, which I wanted because I do all of my fishing in the Puget Sound and I didn't want an open bow of any kind. I like the cabin in my boat so that I can store my fishing gear in there, I can overnight in the boat if I really needed/wanted to, yet there's a ton of fishing space in the rear of the boat, the helm is pretty large and it's a boat that's extremely versatile.

I can go fishing, crabbing, shrimping or I could go sailgating at the Huskies college football game, take the boat to SeaFair, put it in a boat parade, just cruise with the parents and family, etc. There isn't a ton that the boat won't do, and it's more just things that I wouldn't do in the boat more than anything else. I've been out in the boat when we had 4-5' swells and while it was slow going, I wasn't at all worried or concerned that the boat wasn't up to the task at hand. The boat will handle much more than I'd ever want to, and it'll do everything that I need it to do. I bought my boat back in October of 2021 in Maryland for $26.5k and that's about the best price for my vintage of boat that I've seen. I've seen a few other 228 Seafarers for less but they were either older, came with 2 stroke power, no hardtop, trailer or something substantially different. One of which was priced at $20k, though it was a few years older than mine with an Evinrude Etec for power and I don't believe it came with a trailer. Deals are out there, especially in the off season, but in the next few weeks when *knock on wood* it finally starts turning into spring, the prices are going to go right back up to where they were last summer... maybe even more. Do your homework on the boats, listen to other's opinions on here, be patient but also be prepared with cash in hand for the potential right deal to come along and whatever you do decide on buying... have a surveyor inspect the boat for you, if you aren't up to the challenge yourself. Good luck!

Another vote for a Seafarer 228. I've got one, almost upgraded to a Marlin 300, but the 228 just checked more boxes for me. If you know what you are doing, a 60 mile run off shore for tuna is fine in that boat. Just have to pick your days.

I looked long and hard before I bought my 228. It's my 2nd ocean boat and I'd definitely buy it again. For a 22 foot boat, I think it is either the best, or very close to the best, that you can buy. I really couldn't tell you what would be better.

With the greenwood, you don't have the rot but you get the delamination (glass from wood) which is almost as bad as rot. To be fair, you can get delam even with some of the composite materials.
So the build process, materials and workmanship is very important in my opinion.