You can sail a Catalina to hell and back....as long as she's been taken care of. It took me a good six months to bring my boat back up into sailable condition and to properly equipped per the Coast Guard. An older Catalina will cost you next to nothing initially, but over time the price begins to add up. I bought Valiant for $4,000, but by this time have probably invested well over $3,500 into getting her the way I want her. However, by the time you're finished dumping money in (not that that'll ever happen...it's a boat), your boat will still probably cost less than a newer one. It all depends on how badly you want to step back one day, take a deep breath, look at your finished product, and say, "Yeah. I did that." There's just something about choosing built over bought that makes anything feel more like yours.