Having owned a 228 for some years, with an F225 engine, I'd probably stick with a newer boat unless you could find a truly cherry older one. It would hold resale value a bit better if you sell it or trade it in. I got a decent trade in value for mine from a dealer on my 275, even accounting for having lost the engine due to mechanical issues. Used our 228 in Key Largo, in addition to the Chesapeake Bay, and liked its performance in choppy seas. That's why we opted to stick with Grady White when buying a new boat.
I think you can locate some fairly decent 228s or 226s on the East coast, and the prices in this area seem to be a bit more competitive that further west. In fact, my old 228 (re-engined) was purchased by Mustang65, who made an epic trip hauling her home to Seattle (which he documented in this forum not long ago) and he seems pretty pleased with the deal he got from our local Grady dealer, and with the boat's performance so far. Wish they still made the 228, as I'd have bought that in a minute from the dealer.
You won't go wrong sinking a few more dollars into a Grady of that age. You'll get your money back on it some day. Good hunting!