For any apps installed we have an infosec review process the app has to go through before it is installed. We have a separate list of our apps along with an internal point of contact and occasionally (still working out the cadence or audits) will determine if it is still being used. We have to keep a separate list because JIRA does not store that info. You can see the install date but only by going into the security logs and only for 6 months. After that it is gone so we have a separate list we keep.
We can't really monitor usage that I know of (we are on the cloud version). When I was told that I could upvote the Atlassian ticket for this change however it has been around since 2021 so not really holding our breath on that one.
Regarding the maintenance and handling issues we have not really had to deal with that. Yet.
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Don't install any add-ons in production unless you seriously intend to buy them. If you want to demo something, use sandbox. Some of the add-ons don't do a great clean-up job when you uninstall them, and I have found instances in the past where content created in an add-on is still present but unusable after uninstall. For paid plugins, I also make sure that the funding is lined up FIRST, then we do the demo :)
Write some quickie & focused documentation. I have found most users won't engage with external documentation, so if there's something I need them to understand I will put it in a doc in our internal Confluence. For example, we use Structure heavily for quarterly planning and the way it handles filters & groups is..uh...idiosyncratic...so I have a doc which explains exactly what I need my users to know. I always do include links to the external content though for the handful who want more information or when there's a breaking change.
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