The problem I’ve seen is that it often goes more like “do we really need 4 copies, can’t they share?”, “isn’t the 2020 version still enough for 2021?”, or “isn’t that all online anyway?”, and even if it works $300 after overhead isn’t much developer time. Trying to do it sideways like this can be frustrating at large companies because the same place which will pay an enterprise vendor 7 figures to have the privilege of training the vendor’s support contractors will nickel and dime you for less familiar arrangements.
The bigger problem to me is that maybe I could do that for Perl but it’d be even harder to say I need printed docs for every single CPAN module used on a project. Maybe if the core Perl team gets a ton of support they can spread some around but that’s tricky to match to the projects most in need.
That's basically the point I'm making. Paying $75 for printed documentation is easy to justify if your job involves Perl. If four developers work on Perl code, that's $300, which is nothing to the company and a lot better than the $0 they're getting now. Another example would be prioritizing bug fixes and new features.