My experience is to leave some spare time before EOL is reached. Also testing the upgrade on a test environment before you do it on your productive systems is very important.
In my case, I had some troubles with the used Addons and the support was able to help me fixing these. I was lucky we could fix them before we had those problems "published" to all users.
As a System Administrator, this does not only count for Atlassian products, that's how I do Operating System Upgrades as well. Never wait till a Windows Server / Linux Distribution is going EOL and upgrade "last minute".
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