Updating apps bought with 2 Apple IDs

Hi everyone,
My cousin's iPhone 3GS running iOS5.0.1 has apps on it that have been purchased with 2 different Apple IDs.
Should it be possible to do updates to BOTH sets of apps in one operation by going to App Store > Updates and pressing Update All and then entering the password for each Apple ID.  Currently when my cousin does this he gets a message saying "Cannot Connect to iTunes Store."  The error is NOT due to either password being incorrect.
And one further question.  One of the Apple IDs I mentioned above, when you go into the Account area in iTunes, has no purchase history whatsoever (well it does now that I have purchased one test app with the account).  Yet this account has purchased both paid and free apps in the past (I know that free apps show in purchase history when things are working, not just paid ones).  Can any action with an iTunes account cause its purchase history not to show, for example if you change the e-mail address associated with an iTunes account?
Thanks in advance,
Philip

My cousin's iPhone 3GS running iOS5.0.1 has apps on it that have been purchased with 2 different Apple IDs.
very unlikely
Should it be possible to do updates to BOTH sets of apps in one operation by going to App Store > Updates and pressing Update All and then entering the password for each Apple ID.
impossible
Can purchase history not to show, for example if you change the e-mail address associated with an iTunes account?
not as far as I know.

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