You're not getting one program for $385; you're getting multiple programs in one suite. 5-6 programs at $385 or 3-4 programs at $220. For example, Adobe CS Design Standard suite ($220) comes with 3-4 fairly big programs; Photoshop, Illustrator, InDesign and Acrobat. Four big programs - two of which (Photoshop, Illustrator) you're near guaranteed to use at some point if you're doing digital art. Comes out to less than $100/program.
I only focused on Adobe and other creative programs because that is what the OP I was responding to mentioned. My point would still stand if I used engineering/math programs instead of art/design programs.
The engineering tools, especially what you get with many of the student editions are equivalent to programs sold for well over 3x and more than the price of commercial design suites but something that many of the engineering businesses have come to understand is that having students use their products gives them an advantage for when companies choose products. As well as the price difference between engineering software and design software many of the student editions come with large amounts of expensive add-ons for free and this is more than equivalent to a design suite.
The thing about photoshop and the other design items is that they are the de facto standard so instead of treating students as students they instead choose to lower to a still high price and expect students to buy rather than pirate.