The web world indeed can rapidly change their entire stack from LAMP to MEAN to Dockerized Q-Basic CGI scripts and load balance their Twitter clone. There's challenges for sure, but pushing updates is simple and quick, and you can always throw more cloud if you run into walls. If your complete platform rewrite fails, just roll the load balancer back over and try again tomorrow.
It's a lot more difficult when your Python application is communicating with a temperamental motor controller over an ancient RS-232 link with AT commands.
There are only ten of these devices in the world, and three in deployment. They perform critical functions, and they need to run 24/7 without failure or human interaction. (Did I mention these devices are remote, and it takes an afternoon to go out and investigate a failure?)
Every single failure results in a few lines of change in the code base. Those lines cost quite a bit -- both time, money, and loss. It's quite stable now, but that stability came at a price.
But haha, what am I talking about? Geez, I've had ten years to move off this "dead" platform. Let's run it through 2to3, or perhaps try a port to nodejs and deploy it tomorrow.