Things I'd work on if I didn't want to keep this as small as possible for you:
Giving the bot some subscribe/unsubscribe commands, instead of having to go through Herring's interface
Figure out if there's a better interaction model than the high-five, which doesn't work quite as well in DMs as it does in the puzzle announcement channel due to documented Discord limitations
Be smarter about keywords so that they could support short phrases and not just single words
But I'm pretty jazzed about this anyway and I hope you get a chance to take a look.
Things I'd work on if I didn't want to keep this as small as possible for you:
But I'm pretty jazzed about this anyway and I hope you get a chance to take a look.