I can’t think of any problems I’ve faced in over 3 years. I have an app on my phone that I can use to temporarily disable my Pi-hole if I need to do some testing, but I don’t know if I’ve ever had a situation where the Pi-hole was the source of a problem. Definitely not a maintenance headache. I run an update on it every now and then, but only because I see a notification that there is one, not because there’s something going wrong.
“It would be a good value if the value was good, but it isn’t.”