Taking compatibility and price off of the table and focusing solely on the features and interface. Which one do you like to use more? Feel free to explain why or simply just vote. I won't vote until I have had more time with each.
I prefer iWork. I don't do a lot with office documents and its easier for me to find what I need to do in iWork programs because of the nice clean interface. Almost every option I need is in the inspector, and dragging and dropping text is very smooth.
Sure Office has more features but I generally prefer simplicity over features since I am more productive if something is simple. That being said I hate creating office documents so anything that lets me do that faster is great.
Outlook also kills apple mail.
As others have said this is definitely subjective. Outlook in general is an insanely bloated piece of software with a highly inconsistent user interface. (Take a look at signatures, sometimes you have to go into the registry to activate the feature!)
If you are simply a user of Outlook you may not run in to problems, but if you are like me and work in IT I'm sure you've seen plenty of Outlook issues. At every single job I've worked at Outlook has ranked as the most problematic piece of software accounting for the most trouble tickets. Corrupt PST files that you have to wait for it to scan for, the signature issue I mentioned above, out of office replies not sending, etc etc.
That being said it does have far more features, but its also a lot more problematic piece of software.