#Emacs is great. Adapting #orgmode is great as well. It delivers a ton of useful features for my everyday work which I could not do without or with any software alternative.
However, with a sufficient complex setup, upgrading software causes things to break. This time:
28.x
30.1
Currently, tag completion of org headings is broken, linking to contacts is broken (helm-org-contacts), some larger Org buffers can't be saved (without switching to text-mode first), my magit-status window doesn't work and I'm not sure what other stuff is hidden below that doesn't work.
I guess you can't have such an excellent custom environment without that pain.