So whats your solution? We all get that this is imperfect, the question is can the solution be improved upon within the constraints, and if not, what constraints should change?

Because USB-C does a lot and touches a lot of things, I think there's a tendency to place the blame on it (and specifically its cables) for any circumstance where 'plug does not work as expected', which I agree is a frustrating problem that isn't fully worked out.

I bet your HP docks are like Dell power adapters, which only provide specific volts/amps and maybe use some proprietary negotiation and aren't great device-agnostic chargers. I've experienced this firsthand, and unfortunately the blame lines squarely with HP/Dell/your IT department. It's also a sort of 'stage 1' problem in USB-C's rollout, in that manufacturers are used to doing things their way (e.g. proprietary power bricks), and the feedback loop of customer expectations hasn't yet reached a point to pressure them to change. When customers say 'this sucks it doesn't charge my iPad', HP/Dell/whoever begrudgingly realize they need to up their charger game, and little by little the problem is solved.

I think politics might be the best lens to see USB-C through, because USB-C will only work as expected when consumers are providing that pressure. Hence my point about consumer education and clearer labeling being the unforced error of USB-C: moving up the learning curve quicker will minimize these problems and shake manufacturers into offering the thing that meet user expectations and the promise of USB-C. Ultimately someone has to make these things though and manufacturers all have their own misaligned incentives. It's the job of standards to meet them where they are and provide a path to aligning their incentives with better user experience. The reality is it's herding cats.

I haven't seen anything in this thread or other USB-C threads that has offered a solution that improves upon the spec itself that is realistically possible within the constraints USB-C is operating in. That's unfortunate but I think represents the idea that USB-C is, to paraphrase, 'the worst type of connector, except for all the others'.