In all this wonderful generalising let's stop and consider who started this thread, who asked the original question.....
Youmeandthed - A couple in there 20's currently cruising in Panama.
Maybe they are the exception that proves the rule? But come on the Gen Y's aren't all doomed, let's give these guys credit where it is due.
+ freakin' 1. Take all the PRWG pontificating back to The Hole. That stuff is ridiculous.
If more people understood one simple thing (apart from the adventure maxim) a lot more of them would be sailing. And that's this...
It's not that big a deal. If, as a newb on a sailing forum, you learn anything - learn that
You can easily find an old, but perfectly "sailable" boat under 30' for between $1K and $5K. It will need love, but it will sail. With that boat you can have a freakin' blast exploring your bay, coastal hopping, or whatever. Here's over 160 of them:
And here's a specific example of a Catalina 25 for $1950. Sleeps 4-5, looks like it's floating, looks like it has a pretty good outboard, has roller furling, etc.
View Boat Photos - YachtWorld.com
If it is floating, has no serious structural or hull damage, the outboard works well, and the sails are at all usable - this is a freakin' steal. Regardless of how crapped out the interior might be. You could easily make way more than the asking price just parting this boat out. See? You don't even have to "start out with a small dinghy to learn to sail correctly". You can have a small cruising boat like this that you can anchor and spend the night on with a few friends. Then you can even race it if/when you want. How cool is that?
The key is to find a boat that is ready to sail - now. Don't blow all your time and money "fixing it up". That's not nearly as fun as sailing it. Trust me.
Remember, it doesn't have to be perfect, it just needs to be able to safely and reliably get you away from the dock, sail around, and get you back. And as long as you are conservative about when, where and how you sail as you learn - you'll be fine. Just be safety conscious.
And here's the other thing: When you're thinking about picking up sailing for the first time - it DOES look and sound complicated as hell. And, yes, there is A LOT to know.
BUT, it's not that hard. Seriously. You DON'T have to have a stack of certifications to go sailing and have fun.
So, just find a cheap boat that fits your budget (after researching the main things to look out for), buy it, and get someone who knows what they're doing to go out with you a few times and show you the ropes. It's really pretty easy.
I know because this is exactly what I did. I'm still alive, I haven't killed anyone, my boat is still afloat, I haven't had to call in the CG, and I haven't had a single collision or serious grounding.
So just do it already - while these other knuckleheads keep psychoanalyzing society.