In principle, you should be able to make anything work with anything. Failure to do that is the problem of our current technology.

People sometimes have strange syncing needs. Example: I spent some time (and failed, ultimately, due to broken Google Calendar) trying to sync Emacs Org Mode with Android phone. No, I won't switch from Org Mode to anything web-based, Emacs is just too convenient for me. No, I won't switch from SlideScreen to a homescreen with widgets - I love the former and hate the latter. So I need to accept that, right now, I don't have any working solution to sync my phone calendar with Org Mode.

I wouldnt count on it. My experience with outlook is that it doesn't really integrate properly with anything. I'm sure if you're running an exchange server it will sync, but vanilla outlook maybe not.