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Why don't you just use gmail as your client on both machines? If you want to have backups on the machines, you can export to outlook once a month.
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Didn't think of this. Are there any disadvantages to using gmail as a client? I'm taking a look at it now and I'm going to play with the export function but this seems like it may be a good idea.
EDIT: Alright. Now I realize I'm not sure how to export to Outlook. I'm going to keep playing around with this but if there are any words of advice out there I'm all ears.
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If this is a small/personal business, you might want to try hosting your email with Google Apps for Your Domain. See
http://www.google.com/a/
You'd need administrative access to your domain to make the changes, but it's free. And it's easier than configuring replies to not look like they're coming from user@gmail.com. I think they cap it at 50 mail accounts per domain by default, but if you talk to them you may get more.