Re: Seaworthy Sailboat Help!
Zedboy is correct...there are basically (no flaming please - I am talking in generalities about a very subjective subject!) 3 types of boat; racers, cruisers, and blue-water. Every sailboat can do some of each of these; I have an excellent coastal cruiser (i.e. seakindly, comfortable), lose most races (slow), and would not take her across the Pacific. Why? Risk tolerance. The boat is strong enough, and would probably make it, but there are dozens of changes I would need to make to ensure I would survive, say, a major storm. As I always say to folks - imagine you turn the boat upside down and shake it. How secure is everything down below? Anything come loose? Now imagine hitting the sides with a sledgehammer. Plastic windows - nope. I could go on....a true bluewater boat is built like a tank, and tends to be heaver, more solid, slower, smaller inside and more expensive than an equivalent-sized racer (e.g. Olson) or coastal cruiser.
The subject is very subjective. It all comes down to your tolerance of risk. Even within a manufacturer (e.g. Catalina) some models are more suitable to offshore than others - and many would argue (and have) that none are offshore boats!
I have to admit that in your shoes I would look for a solid coastal cruiser, and expect to take a few years coastal cruising to learn the ropes - and then, when you really know what you are doing, upgrade or replace the boat. Sail the Keys or the Caribbean. In your price range a solid 80's coastal cruising (e.g Pearson, Tartan) would be a good choice.