Windows Python Tests

Make --watch-files work in dumb terminals and non-fancy input #721

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Run time

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Job	Run time
build (3.14)	5m 25s
build (3.11)	7m 20s
build (3.13)	7m 2s
build (3.10)	8m 3s
build (3.12)	7m 57s
	35m 47s