I sail alone about 60% of the time I'm out. It's relaxing, good for your body and mind, and a hell of a lot of fun. I generally wear a PFD, and offshore, use jacklines. I don't have halyards run back to the pit so I spend time on the foredeck, but my wheel locks so I can maintain course within about 10 degrees.
About the best thing I've read on the subject is that the superior sailor uses his superior judgement to avoid using his superior skill.
Sailing a '74 Challenger 40' Ketch rig out of San Francisco