I agree with SplashMan.
I have a '97 with 5.0 and trailer towing package. I just bought a Cobalt 262 that is 4700lbs dry plus trailer. I just upgraded from a boat/trailer combo that went about 3500lbs (20' boat with single axle trailer.
Even with the 3500lb combo. I was very happy that I had brakes on the trailer (surge brakes not electric). When you step on the brakes, 1/2 second later, the trailer brakes are engaged and you slow normally (as if the trailer was not really there).
Anything over 3500lbs is recommended to use a weigh distributing hitch with sway control. When you go by a truck (or a truck goes by you), you will be happy you have the sway control. That is on a calm day. If there is wind or hills, you want to try to keep it as true as possible back there. With a 23' boat, you don't have a long wheel base to steady you compaired to a trailer length that will be about 28'.
I'm not sure if I will use my X to pull the new boat. I am looking for a ClassIV with weigh distributing hitch with sway control. I have a dual axel trailer with brakes on both axels (as required by law here).
One of the other things to remember is that you may need a low gear to get the boat out of the water depending on the ramp that you are loading from.
I looked at the stingray web site and a 23' sport boat with that engine may weigh 3700lbs dry + trailer about 1300lbs = 5000lbs. Add gas and gear and you should be OK.