Re: Ideas and/or guidance
Eric, in your situation I might look for a partner with complementary flexibility in their annual schedule. Or, you might find someone willing to 'share' his/her boat on a non-equity basis. I keep an eye on on Craigslist for these kind of options - and what I see runs the gamut from a 16' Hobie Cat in Lincoln, Nebraska to something as nice as a newer Freedom 36' based at the San Francisco Yacht Club in Tiburon. In some cases, a person advertises for partners intending to decide together on what to buy.
Yes, there are all kinds of potential problems involved with partnerships. But the same is true of putting one's boat in charter service. Plus, you might find yourself in a more interesting boat that you can tailor a bit to your own preferences, rather than buying what is popular for charters - like a Jeanneateau with a roller furling main. (Hey, I lease-shared a Jeanneau 40 for a season and it was an enjoyable boat, but if it were my money I'd go for something like a Tartan.)