Re: Grady white 209 escape
Grady's are great boats no doubt. Estimating this Grady is around 20-21' and that is a decent size. However, if your looking to upgrade, you should go bigger and I have a reason for saying this.
If your not into it already at some point your likely to get into bluewater fishing or at the very least having to boat a distance to your fishing grounds. Would recommend a 23-24 and then your done. Would also recommend an enclosed transom and a braket mounted outboard. Gives you lots of room in the back of the boat and when fishing rips or in bigger waves, far less chance of getting water in boat (or worse, swamping boat ). Have seen Grady's w/enclosed transom and bracket--they are SWEET!
I made a similar upgrade from a 20' 201 Aquasport (Center--bay type boat) to a 230 Hydrasport (Center) and love the size, freeboard, room, stability and overall safety of the bigger boat. Interestingly enough it draft's about the same and I can still get into skinny water if wanted.
Best of luck and tight lines!