I think it really depends on where you will be sailing. I don't think you need to worry about "go anywhere" for a first boat. It does not make sense to get a boat that can take blue water when you will never leave the Bay. Remember there are trade offs for everything and go anywhere will mean a boat that likely is not going to move as well in lighter airs, and be heavier, therefore harder to tow.
One methodology is to look at Craig's list find something you are very comfortable with financially and check back with us on specifics on that model. I don't think you can go too far wrong in that size for a boat to learn on. The great thing about CL boats is that they will be really cheap, and you will likely not lose too much if you decide you need more or less boat and sell in a year or two. Also they are boats in use in your area so you might be happy with the characteristics of that boat for your local conditions.
They won't necessarily be pretty, but these boats are pretty simple system wise and as long as it is solid you should be good to go. I think it is not a bad idea to stay with a major maker for your first boat so you can get support from either other owners or possibly the company if they are still around. You can sail the boat for a few seasons, get your scratches on a boat you don't have a lot invested in. You will learn what you really want in a boat and can look for that in the "next one" as there will always be a next one! Normally 3 feet larger, but sometimes a bigger jump. So after two or three seasons you may say I want to bring along some friends and get a much bigger boat, or you may say this is more than I need and turn around and get a Hobie Cat.
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