Was thinking if it would be possible to kinda combine 2 addons to make a new one. The two addons would be:
Tooltip Tabs
http://www.wowinterface.com/download...olTipTabs.html
and
ManyItemTooltips
http://www.wowinterface.com/download...mTooltips.html
The functionality would be: Instead of having many item tooltips open new windows everytime it would open a new tab for the item onto the existing tooltip you have open. If you still want it to open a whole new window you could hold alt or something and click the link to open a new tooltip.