I have been sailing my CS20 for about a year and a half. While I've only single handed her a couple times, I am always thinking along those lines as I trailer, launch, retrieve, rig, reef, dock, and sail. Trailering is a breeze, the boat is light and easy to tow and though my trailer is 8' wide it doesn't need to be that way in fact it would be easier around town with a narrower trailer. I put those plastic bunk covers on my trailer so I can launch the boat with an easy shove. Sometimes I rig the masts in the parking lot before I launch, sometimes I step the masts while floating. Stepping the masts is the trickiest part for me, I leave the sails furled around the masts and lift the whole rig off the boat, spin it, get it vertical, and ease it into its step by myself. The difficulty factor increases with windage and boat movement. The sprits and sheets rig in a couple minutes, drop the rudder into place and you are off. The boat is as simple to sail as Graham says docile on all points of sail, fine in light airs best in medium strength wind. I think it performs well on all points of sail because of its light weight and with its beam it feels stable. I've never tipped it over but I know it will go as I buried the rail and let some water in over the coaming one day.(the rudder had kicked up and the helm didn't respond as I put it over) I've had it planing on a beam reach with four guys on board. I've never been out in even moderately rough seas but I think the boat would handle a pretty good chop well. I would like to make arrangements so that in a reefing situation or in an approaching thunderstorm I could tend the mainsail without spending too much time standing on the forward deck. I love my Core Sound, it's a great design that sails fast and easy and looks good doing it.