As far as Macs go, the company I worked for was 50/50 Mac/Windows, with the majority (if not outright all) of the developers using Macs. We got bought out, and our new corporate overlords were purely Windows, and didn't know what to do about our Macs. Personally, I ended up with a fully manged Windows laptop that I never used [2] for three years before I could send it back and send me a "semi-managed" Mac laptop.
As for Jira, eh. I didn't mind it that much, except when management mandated that every team use the same queue for everything. That queue didn't match our preferred method of working, so we kept our old queue purely for internal stuff. Our time tracking system is way worse than Jira by far.
[1] Not to say I love SVN---I hate it actually, and would prefer to use git. But having used SVN for over a decade on these two repos, and given their structure, it's going to be interesting.
[2] Except to turn it on to have it autoupdate when I got "the email". What a colossal waste of resources. My team kept on using the Macs.
Was that really painful? We did that transition and it amounted to having teams one by one run the "git-svn" script on their repos to port over to git. Even with over a million commits on our central SVN server, the whole process generally took around 5 minutes per project. Even in the worst cases, it was something like 1 hour.
The most painful part we had was putting a rate limiter in place to keep our SVN server from toppling over.
> moving from on-prem to the cloud, moving from Windows to Mac, moving from hipchat to Slack, moving from Oracle to postgres
These are certainly all more difficult but also things that aren't central to the way the company operates AND can be done a piece at a time. Moving from Jira->something else can't really be done in a piecemeal fashion.
The other big problem here is Jira has a wider audience than just the dev department. Dev saying "Let's go from svn to git" is something that doesn't hardly need involvement from the C levels. They never (usually) touch or look at the VCS interface. In fact, the only thing you listed that I think would be a hard sell to C levels is switching from windows to mac. Though, I suspect a lot of them are using macs anyways. Try getting your C levels to agree to switch from mac or windows to linux and I bet that'd never fly in any organization.
> I fully believe that if a project management solution came along and all stakeholders went "holy shit, this is so much better than Jira"
I just disagree. The best counter example is Internet Explorer. Both Firefox and Chromium have been better than IE for a long time (10->15 years). So why didn't every corporation switch to Firefox? Why did Chrome end up winning for desktop web browser even though it came so much later (2008)?
The answer is simple, chrome advertised on media that stakeholders watched.
Chrome eventually won, but it got there through deep pockets and advertising. If there's anything that will topple atlassian, it will have to be through the same route. That product/product set has to be better AND they have to spend a lot of capital advertising so that other shareholders find out they exist. Without doing both those things, toppling atlassian will be a long nearly impossible slog.