For me either:
- Versioning and naming. Framework 4.8.0 -> works down to Windows Server 2012; Framework 4.8.1 -> whoops you need Server 2021. Why.
- Bugs and regressions in its APIs and tools. Most are related to UI and accessibility as you probably guessed.
- VS. It has been slow and bug-ridden for a long time now, but just recently I hit that bug where searching text doesn't find all places. I might have hit it before, but how would you know. It also feels like its tools are sometimes worse than in its previous versions. Suggestions got worse, for sure. But that might come down to my other points.
- Rather ad hoc, unfocussed language design and the problems that result. Better than many others, but still. Not learning (enough) from the past seems to be a common theme in PL design, but it sure doesn't help that it isn't an exact science.
- Anything UI.