I've had an Ensign for about 12 years and have absolutely loved it. I find the cockpit to very comfortable. As I understand it, the boat is not designed to be sailed at any significant angle of heel, so the idea of sitting up on the rail has never come much into play for me. Having said all that, I have found recently that I want to move to a boat with a bit higher performance. Selkie, as much as I like her, can be a bit of a sedate ride.
If you do go the Ensign route, I would absolutely recommend tenting over the cockpit to deal with the lack of self bailing. They can get a bit wet in the type of chop that you'll find in the harbor, but then again I would imagine that most boats this size would as well. Below is a link to one for sail at Northeast Sailboat Rescue. They always have several that are in need of a bit of work at decent prices. They are located in Maine, which may be a bit of a haul, but this one looks like it comes with a trailer.
1964 Pearson Ensign Hull # 57 sailboat for sale in Maine