The taskbar resides usually at the bottom of the screen (at least for 98.4 percent of users). But as widescreen displays become more prevalent (and since I usually have many windows open) it's tempting to put the taskbar either to the left or to the right of the screen. That has the benefit that you usually have longer window captions visible on each taskbar button, especially when there are lots of windows. And at least for me a wide monitor doesn't add much value over one with an aspect ratio of 4∶3. Things like browsing the web and writing code are inherently vertical activities and don't need as much space horizontal (ok, for IDEs like Eclipse or Visual Studio it's nice to have more space but I'd take more overall resolution over more horizontal resolution any time).
Now the taskbar displays tooltips for window captions that are too long to fit:
It does so for a vertical taskbar, too:
Now here lies the problem. While the tooltip on a horizontal taskbar doesn't get in the way very much since it would only overlay a status bar or similar the tooltip for a vertical taskbar intersects with the window content. This usually happens not in a location reserved for auxiliary purposes but rather in the main view of an application:
This is particularly nagging if you restore a minimized window that was maximized before so it begins immediately right of the taskbar. As seen above the tooltip overlays parts of the content of the window just restored. The tooltip appears about the instant the window comes up after a click so it sometimes appears right into content I'd like to see.
Since websites are usually scanned in an F-shaped pattern many websites have a navigation on the left. And I can see that on some regular software, too. The folder list in my e-mail client is on the left and gets neatly overlayed by the tooltip, for example. Since I restore it usually to look for folders with new mail this is particularly nagging, since I need a moment to get the tooltip out of the way. Doesn't sound much and is probably not nearly significant, but still, it bugs me.
Maybe it gets even worse with Aero enabled since then not the tooltip shows up first but rather the thumbnail view of the window which is even larger.
Probably the taskbar would be better off at the right of the screen, since there is seldom information one wants to scan immediately after restoring a window (at least I think so and can't think of counter-examples right now).
UPDATE (2008–11–08 13:56): Activating Aero seems to be a better option than I thought. The window thumbnail doesn't appear when restoring a window and the thumbnail only appears after the usual time, although after the click and not after hovering the mouse over the button as it does when the Windows Classic theme is active.