Calender Sync for Iphone 3G with data from 2 seperate pc's

Current situation:
1 IPhone 3G where personal calender and personal contacts are synced via Itunes to my personal PC at home.
Phone is working on my personal SIM card and is only for personal use...
'Dream'-situation:
As I now have 2 phones (1 personal Iphone and 1 Work mobile (nokia) this is what I want to do (but struggeling to get it to work...)
     1. I would switch the SIM cards and use the 'work' SIM card in my iphone (as my work would pay for the phone calls) and I can close the SIM account that i'm paying for - you know, crisis
     2. I would then like to add my 'work' calender from my 'work' pc via Itunes
     3. Then I would also like to add my 'work' contacts
Now for my questions:
I know for the calender you can have 2 'calenders' - but can you also have 2 Contact-groups (similar to the calender accounts?
Can I then sync the same Iphone with Itunes on my work pc (and only syncing the 'work' calender and/or contacts)?
Can I then still sync the same iphone with Itunes on, my Home pc (and only sync the 'personal' calender and/or contacts?
So in both situation, I would connect the Iphone via cable to the PC's (work or personal); but only want to synchronize specific calenders and/or contacts.
Can I do this with the same apple ID
And who can help me to set this up - as first trials, just erase everything 'personal' when syncing on the work pc...
Thanks

iTunes is not seeing device when connected. It simply freezes (Not Responding) for minutes then fails to see device.
I have previously uninstalled and re-installed latest from Apple 10.2.2. The only way I got that to work was uninstall AMDS and install version 10.0.1 this worked beautifully for ONE Night only. I am now with 10.2.2 that takes 2-4 minutes to start (non responding half of that time the first half just not shown by task manager) and cannot see device. I tried starting iTunes with devices plugged in and same issues. Windows (Vista 32) does see iPhone.

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