> Honestly was it your managers and the development pipeline you hated or was Jira really to blame here?

It was Jira specifically. I've worked in very similar environments with and without Jira, and at a place that migrated onto Jira.

> I will assume you've experienced it used in large projects / environments. What do you prefer/recommend instead?

Trello for the "who's working on what right now" part, even if that leads to having to copy tasks over from another system. For the bug-tracking part... honestly I was happiest using Bugzilla, though I don't know if that even still exists. For the roadmap part, just something like a wiki page, though admittedly a lot of that just comes down to not breaking down your tasks in too much detail too early on.