Thanks for all the advice guys!
wind_magic - I DO realize cruising isn't all margaritas and sunsets. I've read a few books (by L. & L. Pardy and by Annie Hill) - so I realize (at a purely logical level) the amount of comforts being given up. But obviously just "pretending" to do it in your house isn't quite the same.
mikeandrebecca - Wow, that's quite an endorsement. Thanks! (Are you sure you don't own the company?
braidmike - Yeah, that's what I figured would be the best way to learn. It would just suck to jump-in feet-first (what other way is there really?) and then after a month or 2 or 6 decide that you want out. And yeah, the money thing can be scary - it's so hard to get a realistic picture of what's needed - I read stories of people out sailing for years on $1000/month, and others saying they need $4000/month. Obviously comfort-level has something to do with that (ie: refrigeration, water makers, boat size, etc.), as well as how handy you are (ie: scraping and painting your own hull, etc.).
SVAuspicious - Unfortunately, I have ZERO interest in racing. But I get what you're saying... just get out there and start "doing".
I realize there's no perfect way to go about it, no way to know *for sure* how much I'd like it, no way to learn *everything* I'd need/want to know. Well, at least I'm young and single and the "spirit of adventure" hasn't been squashed out of me yet!