Is anyone else having problems syncing iPod after latest iTunes upgrade?

My iPod will not sync after the iTunes 10.4 upgrade - first it tries to reload every song in my library, then it quits and says 'cannot copy due to duplicate file name' and this is while my iPod colored data bar says all the stuff is still there?

It gets worse!  I just upgraded to Mountain Lion and am trying to synch a Mac Book, MacBook Pro, iphone 4s, and two iPads via iCloud.  I have got a colassal unadulterated mess! 
I have now seen as many as 10 duplicates in my various address books and on the web version of icloud.  I tried manually deleting entries from the web version of icloud and somehow lost my wife's contact info. 
I have several email accounts and contact lists I am trying to synch, My .mac and .me accounts, a gmail account, a yahoo account, a commercial account.  I also specified twitter and am trying to add facebook.  I also have an MS/Outlook address book on my Mac's that I am trying to synch up. 
The way that icloud is handing contacts is just a total disaster.  I've been an IT guy and worked with computers for over 40 years and I'm going nuts trying to figure out the logic of what the heck is going on. 
I see a disasterous result of merging data into contacts.  It appears that records that did not match were merged and I have data from multiple contacts in the same record. 
As I said, i have as many as 10 (or more) duplicates in the address book, and in some cases I lost entries such as my wife's!.
What a freaking MESS! 

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