Good suggestion, but not really at all the answer I'm looking for. I'm aware of jump lists. What I'm wondering about has to do with how Windows treats windows and programs that are already open.
Let's say I've got Outlook open and a bunch of mail messages and maybe an event or two, and let's say all of it has been minimized to the taskbar except for a certain message I'm reading. If I navigate away to any other Window - say a web page for this example - in order for me to navigate back to the message I was just viewing I have to make multiple mouse clicks; I either have to hover my mouse over the Outlook icon and navigate to the message I was just looking at, or I have to minimize the web page. What I wish I could do was just left-click on the Outlook icon and it take me immediately back to the last viewed window out of all my open windows under that icon. But I don't want to lose my ability to hover for previews.
Does that make sense? Again, sorry if I'm making this complicated.