One thing worth keeping in mind is change risk.
If you have training created going in to deep detail of working with the Clipboard interface, that training needs to be updated any time there are UI changes. That can be painful.
There are different possible channels for training: web pages, Youtube video, compiled missions, with different costs and difficulty in updating/redo'ing. There would be nothing worse to spend a lot of time creating training and then UI/behaviors change and you don't update/redo the training to stay synced. It is insanely annoying to be following a tutorial and being told click on something and you can't find it. As a newbie, you don't know if the tutorial is out of date of it, you are just missing something. I'd suggest thinking carefully about:
1. Isolate areas of stuff most likely to change from everything else to minimize impact. (e.g. you might want to separate training on the Clipboard to it's own module. That UI is more like to change and cause the training to be redone, than flying and shooting.
2. Put stuff likely to change in the format that is cheapest and easiest to change. Stuff that will need to change often should be in web pages not videos that have to be re-recorded.
3. If you know ahead of time you have big UI/behavior changes on the horizon, you might want to do that first before building training that will then have to be changed.
4. You'll want to think about a process for reviewing what code changes will affect what training so you can update the training at the same time so that newbies aren't being told to do stuff they can't in the UI after a release comes out.
$0.02.
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CptTrips