It's hard to figure out how you'll use a boat and what best fits 'till you get out there and develop your own style.
We wanted the biggest boat our motorhome would tow, so the 208 just barely fit - the 226/228 would be over limit. While the dry weight may only be 600lbs. more, there is considerably more weight with the bigger engine(s), gear, and trailer. Figure at least another thousand pounds or so. An aluminum trailer will help. Here you can see why we wouldn't want anything bigger:
We felt the 208 was a huge investment for a little boat, the bigger boat is even more, and requires more power to push it so a more expensive motor too. But we were looking new or almost new. I could not find a 4-6 year old boat in our region, and wanted the most modern outboard available. I knew I didn't want a ficht!!
Some other user thoughts....
The 228 has a nice live well setup in front of the motor/bracket, while the built in wells under the cockpit seats are marginal. We use a Kodiak 32 gallon mounted in front of the motor. The bigger boat is an advantage there.
We don't sleep on our boat, so the cabin is a potti and storage area. The 208 works fine here, no advantage on the bigger boat. As mentioned, if you're actually going to overnight, the bigger boat has a very slight advantage. For me, it would require something a LOT bigger.
I would not choose a hardtop for a boat that gets towed a lot. However they are great for fishing and ocean work. Something to consider on either size; they are fairly expensive. I put a helm tonneau on and it's very streamlined for over-the-road towing. It's a blessing when it's really windy.
If I was to move up today it would be to a 265 Express or a 272/282 Sailfish. I would just skip everything in between. Otherwise, the 226/228 is just a smidge larger all around than a 208, but basically the same thing. The cuddy serves as a great weather break too, and having spent a couple of years on it would not consider a center console style boat.
Good luck with your search and let us know how it goes. You can't go wrong with a Grady, they are outstanding boats, regardless of what they say on THT :mrgreen: