We are currently planning to upgrade our three Jira environments to version 7.4.4. from 7.2.9.
Or rather, two of the environments will be replaced with new servers, one will be upgraded.
My colleagues believe it is an advantage to install our current version (7.2.9) on the new servers, and upgrade it to 7.4.4 alongside the third server. The argument for this is to ensure the environments are 100% identical.
I prefer to do a clean install myself, to avoid any issues which might be inherited from older versions, and to save time.
A clean install won't contain any of your data - I assume you will want to do an export and import at this point.
An upgrade is going to be easier.
The data is the same as your export/import-on-clean, so that wouldn't get you around any "inherited issues".
In later versions of Jira, the standard upgrade process will help reassure you about "avoiding any inherited issues" - the installer will spot a 7.2 install, and check it for all changed files in the installation, warn you about them, move them to somewhere safe, and then install a clean 7.4.4 and upgrade all the data. You can then use the saved files to replicate any customisations you want to keep into the new one. (The customisations are the "issues which might be inherited" to my mind - I find odd tweaks all over the place on every upgrade. Many are perfectly sane, but need checking before re-implementing)
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