"One day, millions of people will wake up and find themselves locked out of access to a large amount of digital content that they "bought" with the original licensor demanding some additional money to re-unlock access to that material."

Well, we now live in a world of yearly and monthly software subscriptions, so I don't see how the secondary market has any fighting chance even if the license terms we see these days were too onerous for the courts one day as you predict.

Take software that used to be sold in an oversized cardboard box with glossy print (how I miss that smell of a fresh software package), sell it via a created account on a Web site that signs you up to marketing spam, put the word Cloud in the name, make it hella more expensive in a short term contract versus a lump sum yearly payment, maybe throw in an obnoxious tsr that reminds you of updates every two days and pops up ... ta da, Adobe Cloud.

The onerous license terms may change one day, but our wallets will still suffer along with our pride as we pay the Adobes of the world for their killer apps. So, they have to hold up their end of the bargain finally. It'll still be hard or impossible to subvert the loading of the software so you don't need to log in online to use it. I just don't see this secondary market.

BTW, fantastic write-up, thanks! I almost wish I could link to a specific HN comment.