Re: Boat for Single-Handed
Having taught sailing in the Pacific NW, and learned the ropes mostly by osmosis; here's my nickles worth.
The smaller the boat, the less expensive the errors. Make all your really dumb moves in a self bailing skiff like a laser, or topper; they are cheap to purchase, and if well maintained, will sell easily when you want to move up.
Most of my instructing was done on 35 ftrs, as economics force a certain class size 3 or 4 students, hence the need for 4 or 5 bunks for a 5 day cruise and learn. As noted above, not the ideal size to really knock about in, the wear on running rigging and sail fatique with all those slow sloppy tacks, gybes and man overboard manouvers can get expensive when a single sail is commonly costing over $1K. Learn on small boats! Get lots of hours in various conditions, and without an engine, you will quickly learn to read the weather and tide guides after being forced to paddle for a few hours to get in! Also volunteer as crew on as many different boats as you can.
Also re: docking. Rig a midship line, as it can slow your way easily, and gently use your momentum to snug up to the dock, whereas snubbing a bowline will take some paint off, and a stearnline will often be too late.