Here are some thoughts:
1) Cruising is great. Cruising with a family is awesome. You have to get the wife and kiddos on board (both figuratively and literraly). Without them, it is just different scenery.
2) I have sailed out of Oxnard, Catalina Island, and SD. It is a nice area. Nice marinas. Lots of places to go and learn and still be challeneged. I would tell you to do something that sounds really wierd, but is fun and I think the whole family would enjoy (hopefully): Go to some boat shows!! Go sit on boats, walk on boats, talk to salesman and owners. Sit down below on a few of them and imagine yourself cruising. Get the dream into your wife and kids too.
3) As far as sailing schools, I honestly am not a huge fan of them. Two books that no boat should be without are Chapmans Piloting and Annapolis Book of Seamanship. If you really are hooked, you will read them from back to front.
4) As far as the better waste of money (haha), spend it on chartering or trips to boats versus courses. Take your wife and kids on a crewed boat (chartering). If you do not like it in the islands on vacation, you sure won't like it living aboard (though I would take me on my boat over ANY crewed boat... but you get the picture).
5) Hang around here and ask questions.
6) Crewing on a racer is not a bad idea. As a cruiser, it will teach you the n'th degree of trimming sails... but when you do cruise, you really won't care that much as long as they are decently trimmed. However, I doubt the wife will care much for it. The kids might.
7) Be prepared for the very high cos of boat ownership and boat purchase. Better budget in the low 6 figures pretty easily.
You will love cruising. Like SD said, it is not all drinks and sunsets, but it is beautiful. You will become closer to your family and naure than you could imagine possible. It is beautiful, here is a taste....