Right now I have to pull up Pending Changes window, right-click on the file and select Compare->With Latest Version... Is there a faster way to look at my modifications?
You can add hotkey bindings for TFS context menu commands, which may be an approach that will work for what you need.
Go to Tools > Options > Keyboard. In the 'filter' field, type 'TFS' and it'll show a list of all TFS commands that you can bind hotkeys to. The Source Control comparison ones can be shortlisted with "CompareWith". I've bound hotkeys in this way to the pending changes window's context menu, which is a great timesaver versus working your way down that tortuous context menu, but there may be other options that suit your needs better.