For someone who understands the meanings of the terms but isn't familiar with the US parties, "Democrat" and "Republican" parties could also be confusing. But names are often just names, and people tend to figure these things out.
I just read some of the comment history of that account. Is there any way she could be real? The comments look like completely over-the-top, "Everybody hates Jews (and thus us)", insane ranting. Surely people aren't like that in real life, right?
"(number most commonly used words) ^ (number of words)" is exactly what the comic uses. Notice how the words have the same number of bits of entropy in the "correct horse battery staple" example, even though they're different lengths. Did you read it? I believe he also has a "blag" post explaining exactly how he came up with the numbers.
I agree with your link, though, that it's extremely frustrating when websites have policies that prevent certain password options, like alpha-only passwords (even if long) or passwords over a certain number of characters.
To 1, 2, and 3, you are correct. I am also not a fan of his proposal. I tend to believe economies will function better if the government is not needed.
To 4, there is no reason why Kickstarter couldn't work without copyright. There would probably be no tier of "a download of the album", but that's not a necessary tier. Most of the money will probably be made on the physical items or exclusive intangibles for sale anyway. And people still want their favorite artists to create things and earn a living.