Back when I used Win95, Win98, Win98SE, Win XP, I was always bothered by the fact that if you selected a range of files, using the SHIFT key, that the first file would tend to end up as the last file in the list. This was real frustrating when loading music into playlists. It was Jim who made me wise to the weird Windows quirk that caused that. He explained that all you had to do was select the bottom file first, then Shift-click on the top file, and all would be in order. Its a habit that's now ingrained in me.
Well . . . they finally fixed it in Windows 7. You can now click the top file, and Shift-click the bottom file, and all will be good. This is going to be hard habit to break.