Phone contacts and Mac contacts

My husband needed Verizon so just recently got the iPhone although I've had mine from the beginning. The Verizon people transferred all his contacts that he manually entered to his old phone, to the iPhone. We also have a huge list of contacts that are synced to all our computers and MobileMe. I know many of his will be duplicates of our Mac contacts but that's okay if I can make his contacts a separate group which he'll select and I will de-select ... but will this be possible when we first sync?
Has anyone tried merging two sets of contacts and then separate them via groups? Is there another way?
Thanks!

Since you've been so helpful maybe you can steer me in the right direction for me to truly understand the difference (if any) between syncing (between mobile me, my phones, pads and macs) via iTunes settings & device settings and via the mobileme sync preferences & sync now. I've never understood it and I just want everything to have the same contacts and calendars on it but it seems the mobileme sync preferences thing always give me (more than 25%) error messages or tons of duplicates even after I reset sync data. Is there anywhere that explains it? I've been trying to understand it for years!!
MobileMe is a conglomerate of services, one of which is synchronizing between all your iOS devices (iPad, iPhone) and your Mac. It keeps your data "in the cloud" (a buzz term that has been thrown around lately that really means remotely on Apple's servers, not locally on your computer). MobileMe allows you to have all your data current by comparing it with it's master copy on their servers.
iTunes is used for synchronizing your iOS devices only. For those who do not have MobileMe, they can use iTunes to sync their contacts over the USB cable. All data is stored locally (not in the cloud) on that person's computer. If you are using MobileMe already and sync your iPhone in iTunes, it will not even look at your contacts or calendars as it knows you are using MobileMe for this. Think of iTunes and MobileMe as a one of the other thing - not both (in terms of data syncing).
When you "sync now" from the MobileMe preferences it is just referring to syncing your Mac, not your iOS devices. Syncing of MobileMe data on iOS is handled directly through the device itself. As for the 25% error message, that is a threshold that you have set up to alert you that it is about to change a significant portion of your data and a friendly warning asking if you're sure you want to proceed. Before I can suggest how to proceed, which has the most accurate, up to date data? Your Mac or Me.com?
-SM

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