This is why I moved over to Gmail, I was tired of trying to keep different systems in sync and having to mark new emails as read everywhere I went.
So now I forward everything to a single gmail account (and have gmail setup so I can send from it as any of the email addresses I need to), and have all my rules and stuff in one place.
For devices (like my iPhone) I just setup an IMAP client, so anything I do with my mail (delete, mark as read, etc) happens everywhere, and if I send an email it appears in my sent mail folder everywhere.
I used to use Thunderbird as an IMAP client on my desktop, but stopped that and just use the web interface now, but the IMAP stuff worked fine after a bit of tweaking (Gmail has guides on how to setup stuff).
Or if you want to go with Outlook, there are hosted MS Exchange providers out there.
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Uncertainty is an uncomfortable position.
But certainty is an absurd one.
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