help with lifes dream
There were a number of good suggestions as to first boats, plus the caveat that if your experience is minimal to get some hands on saiiing classes first. The charter compmanies are going to want to see the basic certifications before you take their boat anyhow. Sailing different types of boats is one of the best educations you can get.
I''d like to add one more suggestion. Go look at every boat you can that comes up for sail in your area. Look at one, buy a Don Casey book "Inspecting the aging sailboat". Then go look at a lot more. Deliberately look at different types to help you understand what you like, and then WHY you like it.
Try and get to the point that you can look over a boat ,and from your notes give a good overview of what you saw for your spouse.
If you really want to be happy for a long time with the first boat you buy, learn the sport to the point that you understand why the galley is almost always on the port side of the cabin.
Plus, shop Yachtworld like it''s a free education (it can be).
Your first post gave the three kids ages as 14 to 9. You should be able to get significant and productive work out of all by that age.
Our boys 15 to 7 are all productive... even # 3 son can do a half hour on the helm. And our 15 year old is awsome on the water. While we have high hopes for our youngest, his four year old judgement + 40 year old "can do" soul is a spooky combination. He has fun, but no driving for a while.
Youth sailing sumer sessions in Sabot dinghys worked wonders (two week sessions start at age 8 out here).