I run it the same way, just pythonw chirpui if I recall correctly.
I made some changes to kenwood_live.py on my local system (mac) to allow CHIRP to work with all the frequency steps the Kenwood 271/281/471 supports (2.5 Khz was what I was interested in). It works great on my mac and linux machines. For it to work on windows I would need to recompile from source correct?