Re: Single-handed Sailing, So. Calif.
I singlehand my 30 footer without too much problem. I only have to go on deck to raise and lower the main, I have a wheel so I put her into the wind lock the wheel and raise the sail quick, same when dropping it. I will let the main lay on the deck and flake it as I make my way back in. Jib is roller furler so that that makes life easy as do the self tailing winches (which the boat came with) My buddy singlehands his cal30 and it is tougher without the self tailers, but you learn your boat as you go and adapt. It is all about practice and planning ahead, you will also learn what makes life easier and change your boat to fit you.
On the topic of weekending on the boat, I am moving on to mine full time. It is all about what you are comfortable with. Make a list of criteria you want and find a boat that matches. I needed to be able to stand up because I am 6', I have the stove, head, shower, and ice box. I wish I had a chart table but it was a sacrifice I had to make for all the other goodies and to stay in budget. Plenty of people cruise on boats in the 20's, use a coleman camp stove and couldn't be happier. As for the wave size it goes back to your comfort level. Capt. Aaron said in one thread that he likes boats under 30 feet in the ocean because of the way it sits nicely in the trough between swells. Generally you will find that a sailboat is a lot stronger than a person when it comes to handling big water.