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I am not certain that I fully understand your issue. I believe you need to have all of your contacts in your Google Business account. If you have multiple inboxes setup in Oultook and you can see those contacts in any of them, then Outlook will just let you click and drag. Are you able to login to your hotmail account from the login.live.com website directly? This is to see if your hotmail account still exists. Let me know...
Since you have multiple accounts, if you add the 'FROM' field to your emails are you THEN able to change the contacts? Also, is there a reason you do not want to have all your contacts across all of your contact lists?
Do you have the Google Business ACCOUNT set as the default in the accounts list?
I am also going to offer up a remote connection as an additional service here.
There are some things that only really work when it comes to support if I can see it in front of me.
This is one of those things. I mean, you can try this:
If that does not work, I will either have to opt out or remote connect. Let me know...
I an using Outlook 2010 right now. Here is a screen shot of the Address Book Dialogue, the Tools Drop Down, and the Options selection. They are circled.
Have the Google Contacts ever been synced to your local Outlook? What I would suggest is to copy them into a contact list, or to consolidate them, and select that list from the dialogue box. Please let me know if this is not acceptable.
I understand. No money will transfer to me in this transaction. I would suggest, through, that you may want to upgrade to at least Outlook 2013, as that may be contributing to the issue.