Simulating the Windows key on an old keyboard

Remap your capslock key with a quick registry hack? The Caps lock key is worthless.

Paste this into a file called something like remap_caps_to_windows.reg and double click it. You must restart for the changes to take affect

Windows Registry Editor Version 5.00
[HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Keyboard Layout]
"Scancode Map"=hex:00,00,00,00,00,00,00,00,02,00,00,00,5c,e0,3a,00,00,00,00,00

CTRL-ESC brings up the Start Menu.

Unfortunately, it does not allow the other windows key shortcut functions. For instance CTRL-ESC-Pause/Break will not bring up system properties. And CTRL-ESC-R will only bring up Run if you release CTRL-ESC before striking R, and then it'll only work if there aren't any entries in your Start Menu beginning with "R".

You could create a custom keyboard layout with the key remapped.

Microsoft Keyboard Layout Creator may be able to do the job.