Though really, it's not the email side of things that's the problem - it's the complete worthlessness of the address book in just about every desktop email client. Back when I first upgraded to Windows 7 I tried several programs to find that they all have ridiculous limitations, broken import/export, or broken multiple account support.
All I want is an email client that can handle multiple email addresses per contacts (and I don't mean just a "work" and "home" address, I mean multiple), has an importer that actually works, and can speak to more than one IMAP account. Oh, and I want something that's current and nice-to-use - running Outlook Express in XP Mode is tempting, but a poor solution as it's woefully out of date. All of these are not only long-solved problems, but also used to work perfectly in Outlook Express. So why is it nothing today can do this?
This rant brought to you by starting to write an email and discovering that the Windows Live Mail contact