Can't update OS to latest version - get error message

Question

I was getting some advice/suggestions for this problem (see below) from the imac section of Communities, and after several attempts did not work, a contributor suggested posting to the iphone forum. ( I don't know how to cross link)
Problem:
With my 2 yr old macbook, I cannot update my recently purchased iphone 4 when an update is available. I get message: "...device isn't eligble for requested rebuild." I have worked with Apple store Genius bar staff 4 times with no sucess.  Latest attempt was to erase HD, reinstall OS X, and only reinstall itunesin orde to test the update feature.  In this scenario, with only itunes on the macbook, the update is successful.  However, after  I drag and dropped many, but not all, of my programs and files from the saved data on external HD back onto the macbook, and tried an update on a different iphone 4 (in our family plan), same problem.  So I guess somewhere in what I transferred back onto  the macbook is a bad file.  I suppose I could go through the tedious process of transferring one program/file at a time onto the macbook, then trying the update again, but I can't do an update after each transfer because there is no new update to download, as they come out only every so often.
Is there a program that can scan the external HD to find bad/corrupted files?  I have Spring cleaning and Drive Genius, neither of which seem to have the features to do such a scan (they do have disk scan, which I have run, along with Apple's Tech Tool, and all such scan operations have show no problems)
(to complicate this, this apparent bad file on this macbook likely came from my white intel based iMac.  I first discovered this "updating of the iphone 4 problem" on the imac.  When we bought the macbook, we bought one to one and had the Apple store do a complete transfer from the imac to the macbook in its first time set up.  I purchased the iphone 4 in Sep 2010 and first tried an update in Nov 2010, which failed.  I have been back to the Apple Genius bar 5 times since then with this problem.  During one of those visits, Genius suggested trying to do just the update of my iphone 4 from the macbook, and that is when we discovered the macbook had the same problem.  So this bad file likely was transferred to the macbook in that initial set up transfer.  Furthermore, this macbook is still under AppleCare, yet that does not seem to mean anything to the Genius Bar.  Tomorrow I will call applecare about this, but in the meantime, if anyone out there has a clue, I'm much obliged. 
If this works, here is screen shot of the error message:
file:///Users/imac/Desktop/Screen%20shot%202011-07-18%20at%203.21.36%20PM.png
One suggestion was to do a safe boot, then try. Same problem
Another was to provide the contributor a cut and paste of teh Console activity lines of the time this happened.  I did that and found an old version of Mozy still trying to do something.  I fixed that , shut down, started, tried again, same problem.
Any ideas are appreciated. Thanks

Answer 1

Sorry to hear of your woes too. So, do you even get to the point where an error message box appears that  states ... isn't eligible for requested rebuild...", or some other wording,  (with a "more info" tab that takes you to an apple.com  help screen)