[camaraderie]

Livin'...yep. I think you can do it but understand that the risk of getting killed while doing it is probably 10 times the risk that most of us are willing to take. Since you've done a lot of reading I assume you undertsand that...but you know, you only get to read about those that make it! I think you can get a pretty sound, very small ocean going boat for $10k...and if you are handy and willing to work on her for a while...you can probably make her ready for sea for another $5k...including safety equipment.
The one thing I would tell you to do is ...take it slowly. Get out on the Chessie when it is blowing a gale before you find yourself offshore in one. Do an overnight passage offshore in good weather...before you jump across the Atlantic. Better yet...head south in discrete jumps down into the islands and experience trade winds and seas and YEARS of neat stuff to see and do. Cross an ocean when you know what your boat can do and what you can stand up to!

BTW...don't leave without a couple of GPS's and a waterproof box of batteries. Cheaper than a sextant and they work when it's raining! Forget the FERRO!!