Probably worth it to let the Harbormaster know as an FYI, so they have awareness and can keep an eye out. Not a lot of people swim over there near the CG Station (although there's a big, nice beach right there), and the moorings aren't very far from shore, are they? The "I got tired" story...
It's true there are short-term/current gifts to look at. How did they do this year? But I also think good fundraising operations are strategic – long-term. There are a lot of young people who have no real money today, who will be "fresh money" (as you call it) in the future. If you wait until...
Yes, development in NPOs = "fundraising." And yes, they are a profit center amid a large number of cost centers. However, your description of the job ("lots of rich friends...sweet, mellow gigs for semi retired corporate folks") is way off the mark. Being a foundation exec or a sr development...
I second the Rocket recommendation, especially if you can get some practice in on a Sunfish. Get on the Sunfish and then while sailing, imagine a boat that is 40% lighter (or more, if your 'Fish is waterlogged), has a big-enough cockpit and is just as easy to rig and sail.