"Shockingly rich professors of mathematics" - a harshly vertical niche, no wonder the per-unit price is high. But I think they've painted themselves into a bit of an unnecessary corner. Mathematica is a universal workhorse and math has huge applicability. I think they could cut the per-unit price and make it up on volume, selling into commerce and academia. Heck, I'd be inclined to offer "open source user" licenses free for private individuals who agreed to CC license their results and their code libraries.

Who makes more money, Toyota or Rolls Royce?