Does anyone have a recommendation on an online course or tutorial that walks you through doing this type of applied analysis in R? I prefer learning using actual problems, where the complexity of analysis increases gradually.
The Analytics Edge[1] on edX might be what you're looking for. In one of the lessons, they do some rudimentary recreations of the analysis described in Moneyball.
Another course is Sabermetrics 101 https://courses.edx.org/courses/course-v1%3ABUx%2BSABR101x%2.... It's obviously focused on baseball and you have to understand baseball to get much out of it, but many of the lessons on how to map performance statistics to actual game results can probably be applied, at least conceptually, to other sports.