I have used outlook for a long time due to being a creature of habit. I particularly liked the diary element as it was what I used at work and was familiar with. However have been a SAHM for 5 years now. Use my iPhone & iPad for most diary needs but also my laptop (am half considering buying an a mac for this also).
I suspect that outlook is not the best programme to use for diary/email when hoping to cross use the above.
Would be interested to hear what others do?