Very cool. I just copied an item from my personal iTunes calendar to a work Calendar in Outlook. Then the only thing to do is adjust the time as needed. Think it uses the system time as the start time.
Everything copied, except the Travel time, which isn't supported by Outlook, so no issue there.
I'm trying to figure out how to manage two phones, work and personal, where the work phone is highly locked down. I'm able to view my personal calendar in the work phone, but not the other direction. The best option I've found thus far for the two calendar dilemma is that some of the events need to be in both calendars, such as doctor appts or travel dates. Not ideal, but what can do.
This solution from ElKrullo makes it a bit easier.