UPDATE: this 2019 post from Joe Colantonio has a newer list of testing tools for Windows Desktop apps. WinAppDriver, Winium, and White Framework seem to be the best options.
A little-known trick in Windows for arranging desktop windows quickly is to hold down CTRL, select items in the task bar, then right-click: you can cascade, tile, minimze or close the group of selected windows together.
The result is immediately-positioned windows, as you like them. Apparently, this window-controlling feature has been around since Windows 3.1