Speaking of getting in slightly over your head. I took some friends from work on their very first sail one fine, sunny Saturday. It was blowing 15-20 when we eased Oh Joy out of the slip and motored into Burrows Bay. I had full Genny and Main up and the winds increased to 20-25 by the time we passed Allen island headed South. The plan was to sail down to Deception and duck into Bowman Bay to drop the hook for lunch. By the time we got abreast of Deception Pass, it was blowing 25-30 and time to reef since we'd been running with the rail in the water to the winch. Needless to say, running offwind wasn't an option as we were next to a Lee shore without enough room. So, with a rook at the helm for his first time, I furled the Genny and went forward to rig the Solent Stay for the Staysail. Mind you there's no lifelines forward of the sprit's butt and no Pulpit on Oh Joy so hanging out on the pointy end as it makes 15' sweeps while shipping green water ain't exactly fun. I got it done and hanked on the Staysail, not wanting to shred the new Genny like I did the old one. Reefing was problematic since the rook had trouble keeping us head to wind and the boom took me off the housetop once but again, I got it done.
We had a great sail back and the other rookie finally got control of her stomach so we went out across the Rosario to Cypress. The wind moderated back down so I pulled the Staysail, Solent Stay, reef and went back to full canvas. On the return, I hoisted the chute and did a "Titanic" on the sprit while my rookie helmsman enjoyed driving the chute back at 7.5 or so. It turned out to be a nice sail that set the hook for both of them as far as sailing goes. The rook did so well that I let him punch through the tidal chop coming back into Burrows.
I do need to pick up some tethers though. There's been more than a few times when they should've been worn.