It's near lunchtime...
If your mechanically inclined (and enjoy messin about as much as sailing) and the older boat isn't too old and is in decent condition (and the parts that aren't are stuff you can fix) I believe it will be cheaper. Also, you can control the pace of how much you spend by how fast/much your work, assuming it's in sailable condition for the "off-work" weekends. If that's not your thing then opt for the newer, they'll be plenty of maintenance and upgrade wants on it too.
It's kinda like finding a woman, when you see the one you can't quit thinking about just go for it with your heart...it'll find a way to need everything you can spend on it newer or older...and it'll be worth it.
Back to work...thanks for the break.
1982 Islander Bahama 30