I think the analogy holds here.
I think the analogy holds here.
This analogy lost its sway for me with the word 'never'. It's not impossible, in either case.
Perhaps working with a small boat / low-level language is indeed 'harder', so you may be better equipped to deal with the higher-level easier language, after learning the low-level language. Teaching high level languages down to low level languages would be an increase in difficulty, and thus that becomes one logical path for learning. I'm not saying this path satisfies all learning use-cases, merely perhaps the majority in 2017.
I'm not familiar enough with sailing to say whether the same principle transfers to boats...
It's not about easier/harder. It's about responsibility and understanding.
Sailing a small boat is a "full stack" activity, from trip planning to navigation to the low level mechanics of jibing and tacking, even the act of physically keeping the boat upright if you're using a centerboard.
Sailing a large boat usually sees you in a specific role, doing a specific niche thing, and you never get an overview of the whole process.
The same applies to working in a large team of any sort, which is why you see software developers who can't write FizzBuzz but who nonetheless do fine in their particular niche.
-- Programming Pearls, Communications of the ACM, September 1985