Did anyone ran into any issue or have any experience by upgrading Jira SW (Server) from to 6.4 to 8.14.x on RHEL 7.6 platform?
Yes, loads.
Mostly app related, and all found during the test runs. You absolutely must go through at least two steps of upgrade - 6.4 -> 7.0 -> target, and I suspect your test runs will tell you that 6.4 -> 7.0 -> 7.13 -> 8.5 -> 8.14 is the least problem-prone route.
I don't, not any more.
It used to matter when we had Jira 4 and lower versions of 5, but even then, having a wide gap in the release dates didn't do too much harm - systems would talk to each other, but with one recent release and one ancient one, you'd just see a reduced function set, not a total failure.
Nowadays, I don't think you'll even notice much if you mixed Jira 7.0 to 8.latest with Bitbucket 6.0 to 7.latest and Confluence 6.0 to 7.latest.
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