I don''t want to turn you off completely to the Watkins. There are a lot of positives to the boat. It is not a terrible sailing boat, I just wouldn''t compare it to a racing boat. On a reach or run she does very well, she just won''t goes as fast pointing high as some other boats. But then again I can''t point as high as a J-Boat. All boats are a compromise.
Obviously another big advantage is the amount of room you get in the same sized boat. I had a Watkins 27 and its was one of the biggest 27''s out there, and if you are going to be living aboard it might be important to you.
I think the Watkins is a decently built boat, that provides a lot of room for the money. No the woodwork wouldn''t compare to a Hinckley but I think they put the money into a solid construction and oversized rigging.
If you are looking for a shallow keel and a psuedo modified full keel (scheel keel ?) that you wouldn''t be concerned if you beached once in a while then this would be a boat for you. (good for Florida and other parts of the east coast).
To me I think of the Watkins as a poor mans Island Packet. In fact they were built near the same town as the IP''s (Largo, Fl).
If its a good deal then I wouldn''t discount the Watkins, see if you can take her out sailing in the area you might be using her.
(ps....another boat in that size/price range that would be an ok sailing boat with a lot of room might be the 30'' S2 9.2C center cockpit. I know a friend that has one and its not bad for your purposes)