As a user (ignoring fixable things like our admin set up a state-machine for tickets so you can't move story more than one state at a time...) I mostly just hate that the UI is slow and I can't use Markdown like I can in GitHub and Slack
I had the same "state machine" style workflow with something like 6 steps in it. Combined with the slow load times and clumsy interface, I once calculated that it would take me several hours just to move all of my assigned tickets at the time from state 0 to state 5. Fortunately I was able to switch to a workflow that made more sense.
I feel the two types of problems you mentioned form a feedback loop, each making the other more painful.