Take a day or two to do your upgrades once in a year and you'll be just fine. Start upgrading your own plugins as soon as possible, so that you can learn how to

Take a day or two to do your upgrades once in a year and you'll be just fine. Start upgrading your own plugins as soon as possible, so that you can learn how to practice the upgrade steps. Python 2 to 3 was hard for me for the first few codebases, but then piece of cake for the other dozens of codebases I have upgraded.