I'm supposing that there's master plan for a "hosted WooCommerce" service to do away with all plugin management entirely - otherwise, the gain of "one less plugin to manage, though you will have to (etc.)", doesn't seem that compelling.

Specifically: "However, WC Connect does require users to connect to WordPress.com via Jetpack" - this seems to cancel out the main benefit touted, of less plugins/updates/keys (unless you have JetPack already).

I also wonder why, in the long term, shop owners would want to bring in Automattic as a middle-man between themselves and USPS. Presumably, USPS will be able to provide their own service to WooCommerce that does exactly the same thing, using the same hooks. Automattic's will be baked into the default WooCommerce install, of course. But USPS, providing the same service, would have the blessed 'official' status, and no middle man needed, which seems more attractive.

In summary... it feels a bit like this change isn't compelling enough to be something Automattic would pursue - unless it's just one piece of something much bigger.