That would have worked, but it would have made the whole thing a lot bigger— even a featherweight base image would have added more than what pex was able to do. It complicates the usage side too, as then you need to be root to chroot/nspawn/docker/whatever your way into the container.

Definitely a complicating factor was that all of this was meant to be usable by non-nerds and in an environment with limited or possibly no internet access. It wouldn't have been acceptable to download your installer package at the hotel, and then get to site and invoke it only to discover that you were on the hook for a few GBs of transfer from docker.io.

This sounds a bit like a GUI application, so containers would bring their own problems. Also you again force end user install docker etc