I'm pretty sure I've seen it at least 10 times now. I may have a problem.
That said, it helped me get through a (terrible) US Government class back in college. There's a surprising amount of useful information in that series.
There should be a 10x club (support group?). I think I've seen it about that many times, too. My favorite thing is how often Sorkin reuses the exact same lines throughout all of his works. I'm assuming this is 100% intentional, but haven't ruled out the possibility he was simply too high to remember what he wrote previously.
It's the only show I can watch over-and-over again.