I’m looking for these on the right, which can obviously be stacked as well:
I’m sure that this has been asked but I don’t know the name of this feature, and my searches containing
and variations didn’t yield the pages that were helpful.
Would you point me in the right direction? Thank you!
If you just want to change the text this topic may help:
I’m afraid I don’t know how to create a tip from scratch though.
Thank you! There may not even be a GUI-way to do it, but I even missed these somehow. I assumed that these can be created on the admin interface itself with specifying the triggers, but this just means that I will have to look into the source. Appreciate it!
Bumping this up because some guidance would be really useful for my use case too! 
I’m especially interested on having different tips per category - so “Questions” would have one specific set of tips, while “Bug reports” would have another. The instance I work on is on the Business plan, so not self-hosted.
That’d make a great plugin, I’d use it 