What sort of fishing do you do? I looked at a 208 and it is fine for fishing 2 people. It is not fine for crabbing, the deck space is way too small (I'm sure someone will say they can do it but I find my 228 can feel cramped for crabbing). I can, and have, had 4 people rock fishing out of my 228, no way that works in a 208 unless you send 2 people forward. Halibut I do 2 people, you could do the same. Salmon 2 people, you could do the same.
As for the wife, I'd caution you to not push too hard unless she wants to be out there. If she wants to be out there then getting a well maintained Grady is just the ticket. She'll come to trust the boat and I think that is huge.
In the past 10 years, find myself trolling and jigging more than casting. A walkaround or Pilothouse would totally work for this type of fishing. I still love casting but have a kayak and a smaller tin boat for inshore stuff. AFA crew, usually not more than 1-2 guests joining me at a time. Was that because I had a smaller boat for inshore? Maybe… but 4 people fishing on any boat under 25’ can feel crowded (tome). When trolling, 3 seems ideal. Jigging? Does not matter but again, 3 seems ideal again, depending on how experienced the crew is.
Regarding the wife, that is the last priority. I doubt she will go out with me more than once per year no matter what I upgrade to. Her fear is the how level the floor is so even getting a boat up on plane makes her uneasy. Getting rolled by waves triples this for her.
I do value the portability and simplicity of smaller and the 208 would win there. Towing/launching/loading/maintenance , fuel sipping, solo trips, etc. Some of the trips I do are several hours a way. So, off the water value - this is the easier boat.
However, the 228 with that bracket, closed transom, and perfectly positioned livewell are all selling features to me. The extra room and size would also be nice for linger days and greater distances. I’d go offshore more than I have, so there’s that. On the water, this is obviously the winner.
I’d also like something newer so compromise may be needed get something turn key.