This is a great thread. I didn't even know I wanted to go cruising until I met my husband--I was a very happy camper on my little sharpie sailing coastal Carolina. Now we're going together, but late in terms of our ages. We bought a big boat because I had my auntie living with me (you can read about her and us on
www.seaventure.us .) She's the one who taught me to sail. And we had a son still at home. My aunt died and the son is away at college, and we still have a very big boat.
But that's okay. I discovered that I can sail 50' as well as my 18' sharpie. It has tons more issues in terms of mechanics and electronics, but that's where my mechanical engineer husband comes in. And we've made Sea Venture user friiendly for old folk. Michael was a Navy pilot--when we bought the boat he assured me that flying the big planes wasn't any more difficult than flying the small jets onto a carrier. You just have to realize the spacial issues. On Sea Venture, I can't fend off a zillion tons of boat, so we have to think of stopping distance and turning ratio. It works.
We didn't have a lot of cash, so we bought old in Mexico and had a lot of work done on her there. In the last two years, Michael has been rebuilding a lot of things I wanted to change to accomodate my height and to make me comfortable. Now, we're going, ready or not. If the CA house hasn't sold by November, we'll rent it. If all the things we want to do aren't finished, too bad. We'll do them in Mexico or Thailand or on an atoll in the Pacific.
If you have the money to buy an almost complete boat and/or the cash to have it fixed by a yard, then waiting isn't a bad idea. If you need to do it slowly so you can afford to do it right, then you may need to plan ahead as we did. We've been frustrated that it's taken this long, but all things work together for good--and we've had a lot of opportunity to do some good for others while we've been here. And M. is a perfectionist. When he finishes rebuilding all the systems, he'll know them, and know they're done right. That's a very comforting thought for both of us.
As not-so-young, the health insurance folk want huge sums, but we've found international insurance that we can buy for out of the country use. Our biggest expense will be boat insurance, but, hey, it will make us sleep more peacefully.
My son plans to cross the Pacific with us and do some island hopping before he jumps ship to spend time in Japan. He graduated from UNC this May and hasn't a clue what to do next with a political science degree. What could be better than seeing a little of the world? Joshua was home schooled until high school, where he finished as valedictorian. Home schooling done right is wonderful preparation.
Blessings to you and good sailing!
Normandie