I think a large part of the problem with JIRA is that there's simply too many options - they're trying to please everyone (and his dog) which just ends up creating about a trillion possible horror configurations for every sane configuration.
I've recently switched to an ultra simple workflow, fields, statuses, etc. - and don't really hate it so much anymore. But the thing is, a tool with about 100 times fewer features could have done exactly what I'm doing with it. And it took 4+ years to work out the details.
So who's winning with a tool like this really?
It just seems, in trying to make it right for everybody, they actually managed to build something that isn't right for anyone at all, because it's simply too complex for most people to understand.
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