I went from a 22 to a 33 and single handed both of them. I thought the 33 was easier because it didn't react as quickly to changes in sail shape and allowed you to slow things down a bit and recover from tacking the boat and trim the sails without laying the boat over. If the boat is laid out correctly for single handing then you will have no issues and actually be a bit more relaxed. Docking will always be more difficult with a larger boat simply due to the inertia of a heaver boat. Anchoring will be the same.
Hi Dave, thanks a lot for the response.
Anchoring I am sure you are right, I know I will be moving up from line and a relatively small anchor to chain and a much larger anchor. I have had an easy time with anchors so far and really haven't been in any bad situations. If the anchor wouldn't come up I was able to move the boat back and forth over it by just grabbing the line and giving a good pull until the boat drifted over it, then pulling again to try to pry it up off the bottom, things of that nature. Usually I could just grab the line and strong arm it off the bottom and pull it up by hand. I know things are going to be a LOT different with chain and a much larger anchor, that I will need mechanical advantage to do it.
You said docking will be harder, I believe you. I don't know in what ways it will be harder, but I think you are right that it probably will be harder.
I'm surprised that you said handling the boat on the water wasn't more difficult. For some reason I was thinking it was going to be much more difficult. I don't have any experience with a mid-30's or larger sized boat so I really have no idea at all.
Edit, thanks to you too Freesail99, you posted while I was writing my response.