I have an iPad 2 running iOS 4.3. I haven't upgraded to iOS 5 yet as I want to be cautious and I need some advice.

I sync my pad using iTunes at the office since that is where my contacts and calendar data is most critical (using Outlook). I have Win 7 there. I don't sync any music or video there since I don't keep that stuff on the office machine. I do have music and video on my home machine running Win XP and I have used the iPod capabilities on my pad to load audiobooks and music from home via iTunes.

When I am at the office, I use my pad on the enterprise wifi. My office machine is hardwired to the network and not on the wifi directly. I am about to get a new machine at home that will run Win 7. I have wifi at home now and will have after I get a new machine.

If I upgrade to iOS 5 can I sync to the office machine wirelessly? If so, how?
Should I wait until I get a Win 7 machine at home and then sync my Outlook files regularly from the office to home by exporting and importing the .pst files and then upgrade to iOS 5 and sync my pad to the home machine?

Any suggestions would be appreciated!