It must be worth it to me because I've had a slip in the same harbor for over 35 years. At $14.44 for a 40 ft. boat that's a pretty (about $570) penny. So why do it?
It's easy. Yes, maitenance is more, but for that size boat, trailering ain't an option. I'd get a smaller boat but I love the luxury of the space, the safety of a larger boat in the ocean, and the way she handles. I've got lots of labor saving devices (some that I've put in over the years), like electric jib winches, and main furling and well, it's a long list. Bottom line, If I want to go sailing, I just go. It takes about 15 minutes to rig up.
It's fun. I have so many friends at the harbor. If I'm feeling social, there's almost always someone around to talk with, or ask for help, or to go out on a sail with. Lot's of times, however, It's just me and Lisa, or just me. If I don't want to socialize, I just hang out on he boat, or take it to a nearby anchorage, and just hang. Which leads me to the next point.
It's got lots of options. We go out for lots of daysails. Single hand, Lisa and I, taking out friends or family. The boat is so accessible. We can go home, or hang out for an hour or two or all night. Some days (like today) we might not even go out, but just hang out at the dock. Want to take a few days and hang out in Monterey or go up to Half Moon Bay? No problem, the dock is waiting for us when we return. Perhaps a trip up to San Francisco? Sure. Might even sub-let out the slip and say there for a month or two.
It's simple. We live about 5 minutes away. (That is really lucky for us.). After I type this, I'm going down to the boat. Well, maybe after lunch. I'll just clean the boat up a bit and then read a good book for a while. There is a small craft advisory, and I don't feel like taking the boat out, so it's a low key day for me.
A little edit for you all.... I got down to the boat and the wind had died, and the sun was shinning. Yes, it took me 15 minutes from walking onto the dock to backing out of the slip. I went about a mile offshore and found about 15 knots of wind. I sailed with just the jib - what can I say, I was in lazy mode. Sailed about an hour while eating a late lunch, and had a total gas. Hope you had a good day too!!
This post has some points which reinforce how "circumstances" inform these decisions.
Living 5 minutes from the boat is a sort of luxury for most. Closest I've ever gotten is in water winter storage about 15 minutes away. Day sails become very possible and "seductive".
The further from the boat you live the less likely a day sail becomes or just driving down to have lunch in the boat.
But once you are faced with a trip of over an hour say.... what are the differences between a mooring and a slip?
mooring: you still have to get to the boat
slip: you walk right on
mooring: peace and quiet and isolation (relative)
slip: you have to deal with noise, light and neighbors 5 feet away (no solitude)
mooring; quite inexpensive
slip: rather spendy
mooring: less convenience for projects
slip: more convenient for projects.