A most unique mindset.
And hard? Can't get a girlfriend and ostracized by part of the community? Yes thats bloody hard!
The videos excellence touches on those two points: "If people think I am a dirt-bag..." and lack of relationships is a delightful, tender way intermixed with beautiful 'enviable' lifestyle shots. But remember those 'enviable' moments, like thee scrubbing of the frying pan over the side ain't so enviable in real life. Or having worked hard all our lives to be able to, in retirement, cast off the lines only to be thought of as 'dirt bags'.
Good on him and lets hope his cruise goes well and he utterly enjoys it... but lets not take this video as a "What to Expect" 101 because its not, the video is a glorious piece of art depicting a unique person, thats all.
two things i think you are missing:
1) i don't get the impression that he gives two hoots if some people look down at his life choice....anymore than i would. that kind of thing is only an issue if you judge yourself by the judgements of others. i am sure he meets plenty of people that don't think he is a terrible person. i noticed he was socializing with locals in the video.
2) he didn't say he couldn't find a girlfriend. what he said was that he was afraid that, if he did, she wouldn't like the lifestyle and try to drag him back ashore. in other words, he chooses not to get a girlfriend, at this point in life. there are women that love living aboard. one of them posts videos on youtube.
this guy just needs to find one of those women. but, is that really different than any lifestyle you live? if you are a biker, you find women who like motorcycles and motorcycle events. if you are any kind of sailor or boater you find a woman that also enjoys that.
the guy who does the pirate lifestyle videos on youtube used to be a successful business guy with a big house, nice cars, a motorcycle, and even his own small plane. he was married and his wife was used to that 'successful' lifestyle. he gave it all up and they moved onto a sailboat. last i watched his videos, they'd been doing it for 10 years. he didn't have to give up female companionship to follow his dream lifestyle.