If I press the Win Key + a number I can switch to or open the program pinned to the task bar. This works up to 9. If I want to get beyond 9, and into the double digits what do I press?
According to Microsoft Support, it seems 10 (0) is the highest you can get:
Windows logo + number
Start the program pinned to the taskbar in the position indicated by the number. If the program is already running, switch to that program.
Another trick you could try is:
Windows logo + T
Cycle through programs on the taskbar with the arrow keys.