Of the 2 I lean towards apple's approach. And have been doing it for a while using MS's LiveSync/Mesh/whatever the name is this year.......
I have an iPad an iPod touch, a Windows 7 PC and laptop, and a Windows Phone 7 device. So I have already had to create a patchwork of things. Right now the MS stuff is good for me, but I will try out iCloud. I may like it. I use google for mail and some calendar. MS for syncing documents. I use iTunes for music. I have a bad feeling about trusting any one source for all my stuff.