I bought a pristine 1999 Cat 250 Wing Keel two years ago. I picked wheel steering so I could stand while steering. It's less of a pain in my neck that way. You can also sit behind or on either side of the wheel. Standing you have a better view and are unaffected by boat movements. Not so with a tiller. There are several versions of the wheel steering linkage. Mine has a push-pull cable which is not as good as the open cable system that can be retrofitted. (See
http://pages.suddenlink.net/arlyn/sailing/sailing.html Arlyn is the recognized guru when it comes to Cat 250's. He's the inventor and supplier of the steering upgrade.) I will concede that the tiller is better for feeling what is happening and absence of slack in the steering. The other downside to the wheel is that the cables of the split backstay make you have to squirm thru a narrow spot to go forward, on either side, from the wheel. That's why some C250's have been changed to a single off center backstay. I would not recommend that. There's less usable seating with the tiller. I would not trade for a tiller even though my primary use is racing.
It's a relatively light boat (4200 lbs.) that I have read is not well suited to central plains states where wind in the teens is the norm. But it does handle winds in the teens much better than the MacGregor 26D (water ballast) I previously sailed. I really can't predict how it would do in the Gulf of Mexico with big swells and waves.
A racing competitor with a newer water ballasted Cat 250 can't come close to my boat in speed and has about 5 inches less cabin headroom. I would not get the water ballasted version unless it is to be stored on a trailer. The WK is not easy to load on a trailer.
The wide open cabin (no bulkheads), enclosed and adequate sized head, and queen size bed under the cockpit are big pluses. With the Wing Keel version plan on putting about 80 to 100 pounds of pebbles or other ballast as far forward under the V-berth as possible. It's needed for good handling. The 250 has more width in the cockpit than the predecessor Cat 25. I suspect the Cat 25 is bit more seaworthy but a bit less comfortable.
There is a good Cat 250 forum at
http://www.catalina-capri-25s.com/forum/forum.asp?FORUM_ID=4