(1) This sounds brittle. Are you really going to have a good mental model about what's secret when using ssh and reliably refrain from typing those things? Seems to kinda defeat the idea of securing the channel. Also, as a collection your activities might be more confidential to you than single inputs, or correlated with your other activities outside ssh, etc - it's hard to keep a mental model of this as well. Aka optimism is not a form of security.
(2) There isn't a reason to think this is a difficult attack that only a powerful adversary could mount. Seems like a college lab level thing to me. And very amenable to AI help as well. Also here optimism is not a form of security. It's a 25 year old attack[1] so there's a lot of existing research[2] around.
(3) Saving 100x bandwidth on single keystrokes on an internet dominated by video traffic just because it's 100x doesn't make sense. Also it's good to cultivate a mindset that steers away from trading off security in favour of trivial resource savings.
[1] https://www.usenix.org/conference/10th-usenix-security-sympo... (probably older stuff exists outside open literature)
[2] eg https://crzphil.github.io/posts/ssh-obfuscation-bypass/