Hi Scott,
1) Last year I ran everything locally. So, participants submitted their bots and I set everything up in a few local machines to run all the games.
2) There is a lot of flexibility there. The machine I plan to use is going to be dedicated to this, so, I can install anything that is needed. The one thing is that it currently does not have a GPU (waiting for NVidia to have those GTXs back on stock, but not sure when will that happen!). I am planning to run everything on Ubuntu, but I can install any Python version that is required by your bot. If I don't get GPUs on time and you need them, I will need to come up with a plan B
3) Right now the game does not send any notification about that. But if that is something that would make your life easier, I can easily add a "gameOver" function to the AI class, and a corresponding message to the SocketAI class