Taking out the autobiographical nature of the rest of the post, BL is simply saying that some people live on boats. One subset of that 'some' have enough money to do it in a sustainable way, and another subset of that 'some' don't have enough money to do it, and can't sustain the lifestyle.
CF, this is no different than saying some people have enough money to buy homes and look after them while they live in them, and some people have enough money to buy homes, but not enough to look after them while they're in them. I don't take that to say I was born with a silver spoon in my mouth if I own a home, just that I have a plan (income or savings) to do it 'properly' (if the societal norm of maintaining your house is indeed proper), and if I don't, my home will fall into disrepair.
I'm not sure that anybody who truly believes that the latter in either case is a good plan, can be disabused of that notion by reading BL's post (but I'll be damned if he hasn't tried really hard to enlighten them).