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As far as getting familiar with current teams & drivers, I think you'd be safe to go back maybe 5-10 years. Most of the high profile teams and drivers are still around, and it'll give the most recent races some helpful context.
Something like oh so and so is a big name in this race series with some big achievements, but they've switched series/disciplines and that's interesting to watch unfold.
I'll also add that the Truth in 24 documentaries make for something interesting watching. They're a little too focused for following multi-class racing, but they definitely show how to make the most of a story-line within a race.
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