I have three experiences. The first time I was asked to join a war, I didn't really want to join, so I figured I'd ask for a ridiculous number of claims, they said yes, and I was like "huh ok".
The second time, I'm like "ok, I'll ask for ALL the things!" and then they also said yes, so I wrote this thread.
The third time, I decided to see if I could ask for every claim and maybe some cash as well, and they said something like "no that's too much cash"(it was ~1000).
On a related note, I tend not to like diplomatic style mechanics like this where it is a mystery what the AI will respond with or why. What would really make sense is to show some threshold that can be reached for asking for stuff, so you know if they will agree before you send the request. Sometimes game developers push back on this because they think there should be a 'mystery' to it or whatever, but that's pretty much always wrong. It's frustrating to the player because the they get no real sense of why the AI is agreeing or disagreeing with the proposal, and it can give the impression there's no real logic behind it at all. Maybe the AI accepts request up to 100$, but thinks claims are only worth 1$? Who knows! All I can tell you is the results seem bonkers. And requesting every possible claim should never be close to something that gets accepted.