That's rather a large jump in versions, and there's some hiccups.
The best thing you can do is plan for doing at least two phases as the absolute minimum you should to is to take 2.10 to 3.5 and then 3.5 to 5.x - it's really not funny trying to upgrade 3.4 or below to 4 or 5 without going to 3.5 first.
Basic principles though:
- Read all the release notes and upgrade instructions for each step. 2.10 -> 3.0, 3.0 -> 3.1, 3.1 -> 3.2 and so-on. You'll find the upgrade instructions are quite similar, and you need the release notes just to make sure you understand all the changes you will experience
- Test it. All of it. On test kit, obviously
- Watch out for plugins - each one that is not part of the core bundle needs to be checked for relevance, compatibility, licencing and upgrade process. In most cases, the best upgrade route is to actually disable them, upgrade the core data and then install the latest valid versions, but that might not be true for all of them. You may find some won't work on later Confluences, in which case you'll need to work out how to live without them. Some may no longer be needed at all. Some might break in spectacular ways.
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