Review the following:
Delete the OL tif cache contents
https://social.technet.microsoft.com/Forums/windowsserver/en-US/a99d4f1e-26da-4b34-96b1-856990daa743/outlook-2010-not-displaying-images
Note, the above worked on Outlook 2003 which was showing not the red x but a black x placeholder.
http://www.slipstick.com/problems/red-xs-in-email/
http://www.addictivetips.com/windows-tips/outlook-2010-download-images-automatically/
Below page mentions Microsoft's change in html rendering between 2007 and 2010.
http://windowssecrets.com/forums/showthread.php/143697-Outlook-2010-doesn-t-show-pictures-in-HTML-email
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