A bit harsh I think.
My "real freedom" may not be your "real freedom." I kind of think it's relative to each of our personal experiences. And unless someone is actually in a position in which he or she has to test their "intestinal fortitude" who am I to say that anyone can't do it? Everyone has their own bar at which their envelope is pushed.
I have plenty ex and current military in my family and circle of friends and I thank them for helping to create a society that allows me the opportunities that in turn allow me to hire a captain to sail my pathetic drunken ass in the BVIs with in-mast furling*.
*Just an example. I captain my own boat, never sail drunk and in-mast furling isn't on my wish list.
* yes, just an example... and honestly, I have roller furling, not hank-ons at the headsail so I can't really make any headway with that arguement either. But I can distill my rather caustic argument regarding people in my age bracket, call it 25-35 - people older and younger down to:
A) sailing is bit too inconvenient for most
B) weather is too frequently present, as in- there is "weather" outside
C) seriously misplaced values, instilled by a society that has faded to a shadow of it self- lest we forget, once we (USA) were a nation of independent, westward expanding, rebellious adventurers...
Being more than 3 blocks from 2 starbucks outlets- as seemingly impossible as it might be- is a bit more adventure than most of us can handle these days.
If one charters a 50' Cat with all the conveniences of home, and someone to drive it- more power to them, at least they are out in the wind- that's really the point, isn't it?
Racing LAsers, sailing Hobie cats off the beach, Cruising and potluck dinners, sundowners with the yachties, teaching 7 year olds to feel the helm on an optimist, circumnavigating solo on a 20 footer- theres something for everyone out there- why in God's name aren't more folks picking it up sooner? probably lack of awareness of just how versatile and multifaceted sailing is. It is truly the answer for whatever is ailing you.
There is also an idea that sailing is cost prohibitive- which it is, as is boat ownership- however, it too is misplaced. Most people, in my experience, are totally unaware that there are hundreds of awesome sailboats (keelboats) ready to sail away for under 5000 dollars- the assumption is that "yachts" cost 10's of thousands. Further assumptions are that Bermuda is in the Caribbean, and that the Bahamas are hundreds of Miles out there, etc.
It all appears quite daunting, if you never investigate the realities. How often do we see "it's a buyers market."
People also tend to dramaticize boat ownership. For young people, couples or individuals, as has been pointed out in previous posts, a 26-32 footer is plenty- but there aren't exactly tons of brokers out there , parents out there, college councelors out there, saying "go buy a brand x 29, and sail your ass off for 6 months and flip it" IT's a dirty little secret that you can fly to Seattle, buy a boat for 3500- or less, do a 2500 dollar refit, and sail to SAn Diego, and sell the boat for 5000. The real answer- from a young(ish) person who does it- is that theres' no need to saddle yourself with storage fees, etc- buy the boat, sail it, sell it. Want to go again? fine, do it all over again. If you find your dream boat along the way- keep it and maybe (maybe) get a real job to help support the thing.
NOw- in my experience, what you do see a good bit of is people who are in there late teens, to mid / late 20's who have figured out that owning a boat is more of a hassle than its usually worth, and chartering is pricey- so they just get a job that involves sailing, IE Crewing on big square riggers, or Dive boats, or charter boats, or deliveries. As a "sailor" deliveries are my favorite- gunkholing is alright- but it certainly isnt my social scene- I'm in it for the sailing, and if you need your 1st 456 in the grenadines, or what have you, theres alot of folks like myself out there who are A) skippers, or B) crew. WHy pay for a boat when you can get paid to do all the sailing.
that's at the crux for lots of young folks- who wants to hang out in anchorage, sipping rum with everyones grandparents? Let's get out and get heeled over.