[TASK] Port some type annotation improvements from the Core #522

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Run time

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Job	Run time
Tests (^11.5, 7.4)	29s
Tests (^11.5, 7.4, --prefer-lowest)	35s
Tests (^11.5, 8.0)	29s
Tests (^11.5, 8.0, --prefer-lowest)	33s
Tests (^11.5, 8.1)	26s
Tests (^11.5, 8.1, --prefer-lowest)	39s
Tests (^11.5, 8.2)	30s
Tests (^11.5, 8.2, --prefer-lowest)	30s
Tests (^11.5, 8.3)	28s
Tests (^11.5, 8.3, --prefer-lowest)	35s
Tests (^12.4, 8.1)	36s
Tests (^12.4, 8.1, --prefer-lowest)	1m 14s
Tests (^12.4, 8.2)	24s
Tests (^12.4, 8.2, --prefer-lowest)	36s
Tests (^12.4, 8.3)	24s
Tests (^12.4, 8.3, --prefer-lowest)	31s
Tests (^13.1, 8.2)	25s
Tests (^13.1, 8.2, --prefer-lowest)	30s
Tests (^13.1, 8.3)	30s
Tests (^13.1, 8.3, --prefer-lowest)	35s
	10m 59s