Thanks for the thread, Newport.
Your comments remind me of two web sites I've been enjoying.
The first site is done by the Hacking Family, which is dense and richly detailed about their current and past cruising experiences. The "Pre-history" section tells about their original crewing and delivery experience, and about the purchase of their first tri:
The second site your comments remind me of (about relying on oneself) is done by a Norwegian couple in their thirties who are circumnavigating on a Contessa 26. You should see their latest travel entry about crossing the Atlantic. It's an honest (and haunting) account of the trip, and relying on themselves:
I wish you the best with your plans.