Who says you have to maintain old code? We're talking about simply not deleting it and establishing a discrete semantic for the new version as truthfully, a new version is new content which demands a new name to accurately and precisely describe it. If it didn't it would be like saying different content doesn't produce a different hash.
You're right, there is no obligation to maintain it. I think that misses the point though. The value in keeping the code is to allow the end user to continue to enjoy improvements in parts of the library that don't have breaking changes without upgrading those that do. You could continue to have security patches installed, for example. That value is much less when you don't do basic maintenance implement bug fixes and security patches.
Unless I'm missing something… the answer to that problem is to (a) factor the code sufficiently to then (b) create an abstraction (interface) that backs out the concrete implementation to the specifically desired version/functionality.
Hickey's other talk says hard is relative, and I happen to agree, especially when it comes to naming. The question is to what degree of exactness you can confirm what exists (in problems). That is a function of your degree of truthfulness. So it's "hard" only in the sense it's hard to approach 100% truthfulness. However, I have observed that one doesn't need 100%, one needs to be beyond a certain threshold of effective sufficiency. And according to human history, special, rare individuals are born who do exceed that threshold.