re: First boat: Cal 2-27, Pearson 28 or Islander 28?
Since it is your first boat and you'll probably be doing some work on it I'd keep it close to home at first. You can move it closer to better sailing destinations later. I'm on my second boat, and on both my first and second boats I've been visiting it multiple times per week for the first 4-6 months as I work on projects and get it setup the way that I like. After that my visits trailed off and having it farther away wouldn't be a problem. Boats are easy to move and moorage isn't hard to find when you aren't in a hurry.