I'm on my third season with a 240 and sail her on the lower Severn River and Chesapeake Bay. She points really well - almost able to sail directly upwind. Downwind is another story.... Because there's no backstay, the port and starboard shrouds attach too far aft to allow the main sail to be let out more than about 60 degrees. It WILL go farther, but then the upper sail gets caught up in the shrouds. I don't find this to be a huge deal, though, because sailing downwind generally sucks - no breeze on your face and usually no shade. I hardly ever use the jib because, as Crazy Dave says above, you don't want to heel more than 15 degrees or so. I've been caught off guard from gusts, and it gets uncomfortable beyond that angle. It also throws your passengers around and puts a LOT of stress on the tiller. Speaking of which, under heavy load it does take a decent amount of strength on the tiller to hold the boat steady on course. Your second question is about docking. The first season I was on a mooring ball, and I found it quite easy to glide up and grab it with a boat hook, even when I was sailing alone. The second season, we had a slip but no finger pier. So, we backed her in to take advantage of load / unloading using the stern swim deck. That worked ok except at low tide - easy getting on (gravity); not so much getting off. That winter I built a finger pier, and now all is well. I have no problem stepping from the cabin to the dock - just don't step on the cupholders. I'm on my third set. I can stand on the pier and hold the boat in place by myself using the stanchions or shrouds, even with a stiff wind / tide moving the boat away from me. (I'm 53 years old / in decent, not great, shape) Your final question about moving from bow to stern... No real issues. The winches and sheet lockdowns are trip hazards, and their near the step down from the cabin to the cockpit, but I've never had a spill. The boom works well as a hand hold. The front windscreen is slippery when wet, and I have had a couple of spills there - once while moored and once underway, but I didn't fall overboard. I have moored to a ball, docked (both stern and bow in), and anchored / un-anchored all single-handedly. Happy to answer any more questions.