I am curious about Pi, but my experience with a seemingly more fully-featured Hermes has been endless tinkering and fixing minor issues. Have your experience been at all similar?

I've been using it without thinking much about it for 3 months now. Have yet to run into any bugs or strange behaviors. But bear in mind I'm using oh-my-pi, not Pi. I found the latter to be mostly useless in terms of what I needed for my day to day work. I'm sure I could tinker with it to get it right, but that's literally what oh-my-pi is doing for you. And like I said, zero problems thus far.