Don't know the boat, but it's cute. If it were me (for all that's worth, which is nothing), I wouldn't try to satisfy both needs yet. I say that, because outside of knowing that you're ready to learn to sail and that eventually you'd like to spend time in warmer climates, you're not sure what it is, exactly, that you really desire in a boat. Find one you like that's affordable, buy it, and enjoy it as much as possible. Then, you can get a feel for what's a "must have" for your next one.
BTW, which lakes in Kentucky? I'm originally from there, and ironically, my first sailboat, a USYacht 22', was sailed down from Ky to the west coast of Florida, which is where I picked her up.