Divorce - Free apps need to be associated with ex not me

When he goes to update an app, it wants my Apple ID and password.  Fine when we were together but not so fine anymore.  I know that once you download an app, the Apple ID stays with it.  So, I deleted an app as a test from iTunes and from his iPhone.  Then I went to the iTunes store and downloaded the same app under his Apple ID and password.  Now, when I click on that app in the iTunes App library, it does show his Apple ID not mine.  But, I can't get the app to move to his phone despite numerous syncs.  If I click on the Apps tab on his phone and click the Sync Apps box, his apps will be replaced with what is in the library not what is already on his phone.  I don't want to wipe out anything he already had on his phone.  If I go to the App Store on his phone to redownload the app I deleted, it still shows MY Apple ID and wants MY password.  I did do a transfer purchases from his iPhone but clicking the Sync App box makes me nervous.  I also cannot drag from his library to his phone to try to put the app on that way.
Any advice?  Is there a way to make this easier rather than one app at a time?
Thanks!

Go to "Settings" app (if you can) and got to "General" and scroll down to the bottom and go into "Reset". Then hit the button that says "Reset All Settings"  and then click ok. if that doesn't do anything. try updating. This is not a widely reported problem so if the update doesn't fix it, it may be a problem with your phone.

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