Upload & Sell: On
This for me for the same reason stated. If I have to go back to the RAW for re-export it makes finding it a lot easier.
Exactly. Ideally you want to do it immediately after culling, rename the actual files. The problem if you don't is mis-matches later. I also often provide a black and white AND color version of the same image (depending on the client and the image in question), and I prefer for those filenames to be 01, 02, 03, 04, 04-Edit, 05, 06, 06-Edit, and so on, instead of being all a unique filename if it's the same image.