Oh Microsoft, how transparent you've become...
"And just how users will carry over their Office licences in the "upgrade" was not explained."
That's because Microsoft never really heard of the upgrade process. If you paid for Office 2003 and are looking into upgrading to Office 2007 you can forget about Microsoft acknowledging you as an appreciated customer by providing a discount (no matter how small). No way; you'll just have to pay the full price again.
Now, keep in mind that I'm not judging that behaviour perse. Companies need to make money, so they decide to try and get the maximum revenue, their call.
But please spare me the marketing nonsense about how people can "upgrade" to something else. People can't: people can buy into something else instead.
And as the header says: I think they're becoming awfully transparent as of late:
"“upgrade SKUs” that will let IT bosses running on-premises Office move to cloud-hosted Office 365."
Should be obvious: make something so seemingly easy that an "IT boss" (read: manager who more than often knows more about management than ICT these days) can handle it and chances become very high that the brain cogs start to come up with the bizarre idea that they can actually save money by going 365 because they don't need "those IT guys" to set it up for them.
Of course cost reduction isn't everything. There are also important details to be dealt with as security, continuity and the "total cost of ownership" but not at the moment but while also weighing in scenario's such as: "I accidentally removed $important_document, took me 3 days to build and if I don't have it back in the hour it's going to cost us $huge_amounts_of_money".
365 couldn't care less about scenario's like that, while those "overpriced local ICT guys" might very likely be able to help you within the hour. Of course that kind of service comes at a price, but unfortunately most managers tend to forget that these days.