I would like to know what are the approaches that you use to manage the executables in your system. For example I have almost everything accessible through the command line,
Creating a folder c:\bin adding to your path and hardlinking like you said could shorten the string. Maybe add a variable pf to system vars with value c:\Program Files then replace c:\Program Files with %pf% in path.
Edit:
Create a virtual drive.
subst p: "c:\program files"