Aaron, I just got the time to read this thread - WOW! One thing I immediately noticed is that you seem to have lost some weight. Hope that was on purpose.
As for single handing, I do that all the time, as many of you know - even when I have someone with me. For me, I feel much better when I have total control of the boat and everything in it. Sure, it's nice to have company along, but for the most part, they're mainly passengers, even when they're experienced boat owners themselves. Now, when captain Melissa was with me, I loved every minute. She's a real savvy lady, knows her way around a sailboat better than most I've met, and one Hell of a mechanic to boot. She saved me a lot of grief and a bundle of money when she climbed into the engine compartment through openings this old man could never access, then discovered there was a fuse on the side of the electric fuel pump that had blown. I had already spent more than $300 having a local mechanic fixing things, and the engine still wouldn't run for more than 30 seconds. After she changed the fuse, the engine has been running like a Swiss watch ever since.
Now, Aaron, I won't be sailing back to the keys this winter, but I hope to be driving down, probably in late January, spend a month, then head for a couple other locations before returning to the frozen north. I'll be playing music at some of the resorts and Tiki Bars as well, and I would sure love for you and your dad to come to one of the places I'll be playing, tilt some brewskis and eat some fattening food.
Keep in touch,