We are well into our second year of sailing on a 20' Express. We fell absolutely in love with sailing. Probably went out every day for the first six months, then moved further from the lake so now, only 2 to 3 times a week.
We had a couple of lessons, the rest we learned from a lot of you, books, videos, and many mistakes. The more we learn, the more we understand how awesome, technical, and fabulous, the art of sailing is.
Positively itching to buy a boat and get out on the ocean. We are thinking it would be best to crew for a while before we decide on a boat and go it alone. We are in this for the long haul and don't want to learn "Dumb skills". We also don't want to buy the wrong boat for our needs. We have already been saved from buying "project" boats by this forum

Thanks.
We will want to cruise from the southern Texas coast down to Nicaragua (We have many friends along that route and would like to continue humanitarian aid, we have been involved with for many years, via sailing). We won't need to carry many goods(aid items) with us, except for a few things that can't be purchased locally. We will have children aboard, we are more concerned with soundness and maneuverability than bells and whistles. Comfort would be awesome, but only up until it impedes on safety. Size is a big question mark. We want as large as possible, but want to keep cost reasonable for repairs and upkeep. I hope this gives enough information for some good input. If you were going to sail your wife and children around for many years in those waters, what boat would you get?