That's a fair point, and I agree that both Microsoft and Apple are well within their rights to make their programs work any way they please. If they want to ignore standards, they can. If they want to play together, they can. It's a free market.
But having said that, Apple clearly states that iCloud works with Outlook, including Outlook calendars and contacts. That claim has obviously mislead thousands of Outlook users, myself included. Furthermore, Outlook sync used to work. Back when MobileMe was supported, Outlook sync worked correctly (i.e., the way everyone on this forum naturally expects). So Apple clearly knows how to make Outlook sync, but deliberately chose not to. That's their right, but it's awfully frustrating and a poor business decision, IMHO. I can't imagine what Apple gets out of it, but again... that's their call.
Bottom line: I'm more loyal to Outlook than I am to Apple or iCloud. Say what you want about Outlook's bugs and foibles (it has many), but it's extraordinarily popular and very well-supported. It's practically a de facto standard. If Outlook and iCloud don't work together, there's no question in my mind that I'll keep Outlook and ditch iCloud.