> pain in the ass
Yes, unequivocally.
> frequently breaks
It can definitely depend on what you're scraping, but in the last few years or so the only project I had trouble with was one where they changed the units for the unpublished API (the real UI made two requests which mattered, one to grab the units, and I missed that in my initial inspection -- it bit me awhile later when they changed the default behavior for both locations).
A few tips:
As much as possible, try to find the original source for the data. E.g., are there any hidden APIs, or is the data maybe just sitting around in a script being used to populate the HTML? Selenium is great when you need it, but in my experience UI details change much more frequently than the raw data.
When choosing data selectors you'll get a feel for those which might not be robust. E.g., the nth item in a list is prone to breakage as minor UI tweaks are made.
If robustness is important, consider selecting the same data multiple ways and validating your assumptions about the page. E.g., you might want the data with a particular ID, combination of classes, preceding title, or which is the only text element formatted like a version number. When all of those methods agree you're much more likely to have found the right thing, and if they don't then you still have options for graceful degradation; use a majority vote to guess at a value, use the last known value, record N/A or some indication that we're not sure right now, etc. Critically though, your monitoring can instantly report that something is amiss so that you can inspect the problem in more detail while the service still operates in a hopefully acceptable degraded state.