Did you just say you'd miss the wind in your hair?
The 23' Grady is not really trailerable with a 9' 3" beam. For that reason I went with a 22' Grady when I had mine. The Grady is nice, but for the money, I'd look elsewhere. Look at Sea Hunt, Jones Bros., Scout.
A wide beam doesn't always mean stable. A lot of deadrise will give a good ride (usually) but will sometimes feel like sitting on a log when on a drift or anchoring. Too shallow deadrise can sometimes give a rough ride. Nothing is set in stone with boats though because everything comes into effect on something else. Everything is a tradeoff. You want one feature but may have to give up something else to get it. You need to think long and hard about what you really want the boat to do, set a price range, and get as many opinions and test rides as possible.