Well...I might end up one of those you speak of one can never tell what life will trough at you...but I have 3 girls that i want to put through collage just as badly as i want to sail so there it is..
I have 7 years yet to go to accomplish that...it is what it is...we all have our reasons for what we do...Our goal is different then allot of you cruisers in the first place...in that my wife and I have no desire to sell all and go...we like our stuff and a bit of Terra Firma to call home...We plan on starting out with a 6 mo on and 6 mo off the boat lifestyle and see how that goes for a few years...if it goes buy too quickly then we can possibly try and figure out how to afford 9 and 3 or something like that.
I will never have a so called retirement income
as I am self employed but I can make good coin in a short time if
there is work to be had..this of course will change every year with the economy and what not so it will be what it is.
As far as the need to be so knowledgeable that you are a walking encyclopedia everything nautical I could not agree more that that is an over emphasis often times on this and most all forums
...A good dose of common sense will out perform knowledge 8 out of 10 time in my life experiences if the one with the common sense also has some self temperance and not just bravado.... and some stick-to-itiveness to see something through thick or thin...
I seem to hear about just as many so called experienced sailors needing plucked from the sea as neophytes. ..Im a go for it kind of guy ..always have been...I bought a plane and taught myself how to fly years before I paid for my first lesson to become legal
...taking off and landing on short bush strips in Alaska
...Our need to protect society I think has curbed allot of seat of your pants learning...some of that is a good change some of it sadly is not.
I would not mind crossing an Ocean with someone else for the first time but if my timing says go and their's doesn't so be it...as they say nothing to fear but fear itself.
I will be amongst the first ones to tell young newbies to get some experience and a sound boat before tackling an Ocean crossing
...but I will also be the very first to tell them just buy a 20' boat and go out in the bay and learn to sail it..it ain't rocket science..you don't "need" lessons...if you don't want them...I haven't had one yet ...and I seem to go out and get back in.
In the end its a personal decision as to what your prepared to handle out there without hitting the mommy button..Just don't put others at risk whom you have buffaloed into thinking your some hot shot sailor when your not yet...that's my only real rule
...its OK to drowned yourself learning on your own but know one else...
FWIW..I never took anyone flying with me till I had 150 hrs logged in the bush ...by then I was putting the plane where I wanted when I wanted landing spot on in less then 300' and taking off in less then 600...had weathered many storms with seat of the pants navigation
like they use to do it..hanging your head out the side windows and watching your altimeter and compass
...and some wicked crosswind landings...It was all good and a cherished life experience...Sailing is no different.
So go for it..life is short...and ignorance can be bliss..