When I use to be in 115, we had Google Hangout sessions for 3+ hours for almost seven days a week (don't worry, it was during the summer

). We first started off with a simple WCD chassis, then a single speed gearbox, etc., pretty much basic mechanisms and techniques. To check if anyone was struggling, we used the screenshare function.
The entire purpose of this was to get us familiar with the FRC design process, because in the end, our instructor let us off on our own to CAD without him watching.
I guess the takeaway for me was that CAD trainings should be one where minimal time is put into learning how to use the software, and more of making something. But another important takeaway is that mastering this skill may be a big time commitment, and not everyone may be on-board; out of, I think, 10+ people who attended the training, only a very few came out of the session confident enough to make something that could be used in competitions.
Yeah, just putting out how I learned to CAD. May not be the best idea, but sure is an option.