Sync multiple e-mail contacts

BUMP

Well, you ask tough questions.

I have several e-mail accounts. One Personal, the other business, an other for organizations, etc. I want to sync my address books to my iphone with the following caveats

iPhone doesn't really support multiple address books. The best you can do is use "groups" to organize contacts. Google "itunes contacts groups" and you will find some relevant introductions to the topic.

1) Personal address book (yahoo) only syncs with personal account (vice-versa)

Don't think so, at least at this point. I think you need to have a single, consolidated contacts database, but you may be able to structure it with groups.

2) When I e-mail a client, it knows to use my business e-mail account (vice versa).

Again, not now. You might check out one of the "Groups" related iPhone apps which might help out here (search for "groups" in iTunes store and look at the apps). Note, iPhone software v4.0 is expected this summer, and with it's new consolidate mail program they may have put some thought into how you might automatically select email account when sending an email. But it doesn't do it right now.

On a separate not: Is there an easier way to automate i-tunes to ask which library to use (other than shift when you start)? I do not want to create a separate user account just for Itunes.

Have you tried double clicking on the .itl file? That might do it. And if that does, just create a shortcut to that .itl file.