So little time, so many boats... I'm coming from the world of classic fiberglass keelboats, where so much time gets spent reparing or overhauling 30 year old systems on a 5 ton Tartan 30. The basic hull and structure are sound for decades, but so much stuff on or in it needs looking after. I'm between big boats now, so have time to make a little one from scratch.
I'm painting my Skerry now, so I'll be ready for spring on the chesapeake (although it would have been in the water if ready on Christmas it was so warm). I chose the Skerry because it was the biggest CLC kit I could conceive of cartopping and easily moving about by myself. Also, it was one I could imagine building fairly quickly though it has been 18 months since the start (many distractions...the actual hours aren't too bad). I've had it out once with just the epoxy on it for a check of the rigging, hull, cartopping, etc. Now it's back in the garage, stripped of hardware and being painted.
The NE dory is like the Skerry in that it doesn't have side bench seating which can make long sails more comfy. The SW does have those, much more like what I'm used to on a big boat. If you are going to sail with 2 people aboard, and will be trailering anyway, I'd consider the SW. Yes, it's heavier, but once in the water, that won't make much difference once you learn the boat. It will cope with wider ranges of weather and give you a longer cruising radius, even without a motor.
I'm not a skilled wood craftsman, but the quality of the CLC kits is such that I had less trouble with the skerry than I feared. I had made one of their Sassafras canoes a long time ago and this went together easier. Looking at the SW, there's a number of extra interior parts, but a lot of those will slot together and get glued up in groups. It will need more workspace, though. I am glad I didn't try to shoehorn a bigger boat project into my garage space.
The big time sinks for me are the finishing steps. I decided early on (after my first epoxy fillet goof up) that this would be a "working" finish, also known in some circles as a "10 foot finish" (ok, mine's more a 20' finish). Stand back 10 feet and it looks great. If I took that same route with a SW, I think I could get it together within the same year or so with only a bit more discipline on the project hours. Painted finish inside and out, flattening the Brightsides to a semigloss, and only varnishing the rails and spars, will have me sailing my skerry months before a "piano finish" boat would float. The outside, dark green, looks a lot better than I thought it would with my hamhanded epoxy work. The inside will be flattened Hatteras White and I think it will hide many of the other sins, all of an esthetic, not structural, nature.