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There is a mysterious variable Python responds to, actually!
export PYTHONUNBUFFERED=1

./myscript >> file &

I don't think stdbuf is applicable unless you're writing to a pipe or TTY. Block or...

It doesn't hurt the script or your system to hard-kill it, no -- but it certainly doesn't do what you want.

Python does single writes every 4096 bytes because this more efficient than doing 50...

You have to trap the signal and flush the output file descriptor.

I do not know python signal handling, but you should trap SIGTERM. This is the signal kill sends by default. A generic trap...