I think we all want to avoid accidentally building "Clippy" the helpful paperclip who wont shut up. That is, there's a fine line between helpful and pestering,

I think we all want to avoid accidentally building "Clippy" the helpful paperclip who wont shut up. That is, there's a fine line between helpful and pestering, so I'd wager the default thinking is: "Let's make it really easy for a user to ask for help, but stop just shy of forcing it on them." That being said, when everybody is adhering to the default frame of mind, maybe that's a sign that your product/service could be legitimately disruptive (in a good way). I'd say go for it!