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In Outlook 2003 and 2007, there was an option to choose the preferred message format on a per-contact basis. It's explained here: http://office.microsoft.com/en-us/outlook-help/change-the-message-format-to-html-rich-text-or-plain-text-HP001232996.aspx#BM3
I'd like to find this specific option in Outlook 2010. Can someone point me in the right direction?
1It should be noted that this works differently when using the Outlook Hotmail Connector. If I click on Outlook Properties in the contact card of a contact in my Hotmail/Windows Live account, the dilaog that comes up is completely different and only has a checkbox for "Use Microsoft Outlook Rich Text Format for this recipient". – PersonalNexus – 2012-02-16T19:46:42.080
1Also, if using Exchange, this is not available for those contacts in the same organization as the sender. – CharlieRB – 2012-02-16T19:57:33.027