I think it's not so much about the money as the "When you had to walk into a store... [and] be stuck with it" part. That is, the problem was actually automatic/Internet-enabled updates.

With the physical model you chose your software and it didn't stop working. (It might stop being useful, but that's a different story.) No option to patch later meant a company couldn't ship trash: word would get out and people just wouldn't buy it. (Windows ME, anyone?) Now you can get the rug pulled out from under you on all of your tools, and things "ship" as garbage with a massive "day 1 patch" (and a "day 2 patch" and...) and honestly often never get finished. At least not before they're "retired" and you're "updated" to some dumpster fire that's nothing like what you wanted, and still doesn't even work, and you can't do anything about it.