I don't give any voyeur credits other people are giving him. He's a horrible sailor; a horrible student; a horrible boatsmith; a braggart; downright lazy, and has performed some really really stupid things, some sucking in other people who enable him. I don't believe in luck either. And I don't believe he deserves to be out there. He may be nice, but nice doesn't balance being an idiot. There are plenty of nice mentally ill people.
What I do give him credit for though is for sticking it out. Turning down being rescued from HW to SF for example and then taking forever to get here. Aborting his first attempt to get in to SF that first night and waiting it out till the next day (he totally miscalculated his route). And sailing under the bridge on his own was pretty cool.
If he was worth a damn, he would throw away those silly goals and just go sailing, and work his way from place to place enjoying what comes next in life without any agenda, meeting people, helping them, with some personal responsibility instead of entitlement.
btw: anyone who help him should consider that their enabling is directly responsible for his demise. Possibly legal