I disagree with your analysis.
Before iCloud, Outlook for Mac synched perfectly with Calendar and Address Book. (OK, sometimes you got thousands of duplicate calendar entries, but aside from that, it worked). Then using USB, you could sync your phone and everything was fine.
Once Apple implemented iCloud, it stopped working. Frankly, I don't see why. It seems to me that if Apple wanted, Sync Services could still link Outlook to Calendar and Address Book and those Apple apps could sync to iCloud.
So I don't necessarily blame Microsoft for this. And when this did "work", I definitely blame Apple for the thousands of duplicate entries, which happened to many users when synching. There was absolutely no reason for that because each entry contains a database ID. The system should easily be able to identify the dups.
I'm getting increasingly frustrated over the fact that in spite of the addition of new features, Apple keeps taking steps backwards when they implement new OS versons or new versions of apps. The other thing I find is that Apple's instructions and screen messages, which they really used to refine to make their systems easy to use and understand have become just as incomprehensible as the idiotic messages that Windows provides. And I'm a techie who generally understands this stuff - imagine how neophytes feel.
In addition, the whole iCloud/Apple ID signup process was a freaking nightmare, resulting in IDs that didn't work anymore, etc. And the fact that you can't combine IDs to consolidate accounts is also ridiculous.
There are still reasons to use Outlook over Apple's apps, especially if you're a business person, but even if you're not, the Outlook integration is better between email, calendar and contacts. As far as I'm concerned, this worked before iCloud and there's absolutely no reason why it still shouldn't be working.
To add insult to injury, after upgrading to 10.9 Mavericks, Excel now crawls. For me personally, I'm not interested in a Mac that only runs Apple branded applications. I've used Apple computers since 1980, but they're coming very close to losing me as a customer. But they might not care, because Mac sales are now such a small part of Apple's revenues, they may only want to be a Pad/Phone company.