FWIW,
I'm on a mooring, can come in or leave in almost any wind/tide. Granted no shore power, or convenience of just hopping aboard, but it has it's perks......
Privacy.
Easier to ignore troublesome neighbors.
No BBQ restrictions.
I can enjoy a cigar w/o complaints.
Can swim off her.
$150/year vs $2100.
I use the Launch Service, so it's easy enough. Granted that's $850/year. Some years I forego it and use my dinghy.
Not knocking the slip, I've done both, I just prefer the mooring given a choice.
The 323 is a great boat to single handle, trimmed and balanced right she practically sails herself, so I personally never saw the need to autopilot. If I need an extended head break, I heave-to. For all intents and purposes, I pretty much do it all even with the Admiral aboard. I'm not to concerned not always executing the "perfect" tack either, anything can be corrected and I'm not a racer.
Yes to the aforementioned the safety considerations, jacking, pfd etc...mandatory. I use an auto-inflate pfd on the chance I'm "boomed" overboard. To reiterate, a great boat to single hand!!
"Sub" Ed