[BoardsOfCanada]

I don't see how "More people have been to Russia than I have" can initially seem acceptable. I assume it's being parsed as something that makes sense, but what is that? "Many people have been to Russia, but I haven't" or what?

[IIAOPSW]

"Number of people who have been to Russia" is an integer. "I have been to Russia" is a boolean. Is 5 > True? Depends on what language you work in. Is it useful to overload "greater than" to apply to numerical and booleans like this? Sure. It is not I alone who has been to Russia. There's a great multitude of people who have been to Russia and could tell you more than I could. More people have been to Russia than I have.

[gryn]

you can parse it as 'I have been to Russia' => integer representing the number of times you've been to Russia.

with the original boolean meaning being a special case, and this being a context-dependent generalization to be inferred by the listener.

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this kind of sentence would kinda make sense (in the sense of being informative to the reader and not just a tautological statement) if you, for example are a researcher who have access to a native island where most people are forbidden from entering and have been there multiple times since you were given an exemption from the rule.

here is a list of islands you probably wont have access to: https://en.wikipedia.org/wiki/Uncontacted_peoples

[tux3]

My initial parsing is "than I have" -> number of times I've been to russia, so this'd be comparing the number of people who went to Russia with how many times I did.

Nonsensical, but that's my initial intuitive parse