Thanks for the feedback!

1, 2, 3 and 4: definitely doable 5: tricky, probably impossible to do reliably 6: doable 7: without any manual interaction this could end up looking spammy. If you're happy with that, it could work.

Also forgot to ask what platform people would prefer: Android, iPhone, Windows, OS X or Linux? Platforms like Messenger and Slack are probably out of the question unfortunately because the bot would have to be querying Google automatically, which is more reliable from your own IP.