I don't think this is going to really be a thing, aside from fairly specialized use cases. Some devices with integrated cables are going to require adapters (and, fortunately, an A->C adapter is tiny, or carry one of those Anker 4-port USB hubs that's the size of a pack of gum), but I'll just buy new five-dollar cables for my type-B devices and not really care too much about it.

Having to re-buy all of them is a drag, I am totally not saying that doesn't suck, but I'm not worried about having a bag full of them.

At some point we have to agree on a standard railway gauge. The transitioning phase will be painful but the advantages are worth the switch.