Test Flags

Convert all remaining type annotations into the modern format #4986

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Run time

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Job	Run time
Flags (3.14, ubuntu-22.04)	3m 0s
Flags (3.7, ubuntu-22.04)	1m 32s
Flags (3.12, ubuntu-22.04)	1m 55s
Flags (3.9, ubuntu-22.04)	1m 45s
Flags (3.13, ubuntu-22.04)	3m 21s
Flags (3.14t, ubuntu-22.04)	2m 54s
Flags (3.8, ubuntu-22.04)	2m 10s
All Flags tests passed	2s
	16m 39s