accessing windows outlook file on mac & issue with palm

This is technically two problems but one basically spawned the other.

1) I was able to connect my palm and sync correctly after doing a hard reset on the palm. HOWEVER after I restarted the computer I wasn't able to sync again (no changes in settings and I checked the one setting in parallels that I thought might change back.) I don't want to have to hard reset each time I want to sync the palm... any clue why this might be happening? Windows XP Pro with a Tungsten E and never had any problems when I was syncing to my real desktop pc.

2) I was looking at ways I could maybe forgo the pda and get all of my contacts and calendars on my ipod. I found a way to do it if I synced itunes where I have the program I used for contacts and calendar - this:
http://docs.info.apple.com/article.html?artnum=305508

I've been syncing my ipod on the mac and using outlook in parallels (winxp pro also.) Is there any way to get access to the outlook info with itunes without switching my itunes set up over to the pc side of things? Maybe I can make this one fewer devices ...



Other things to keep in mind for future parallels builds (not exactly requests):
hamachi (i would love to have access to the hamachi I have installed on the pc side since it's not as easy to get it installed and working seamlessly on the mac side of things ... if mac and pc side shared the pc hamachi ...)

various syncing (palm, windows mobile, ipod, cell phones, other network syncing)