Run dependency tests

Handle expected boolean values for waiter error matcher #990

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Job	Run time
build (3.8, ubuntu-latest)	1m 47s
build (3.8, macOS-13)	4m 8s
build (3.8, windows-latest)	10m 44s
build (3.9, ubuntu-latest)	1m 51s
build (3.9, macOS-13)	2m 57s
build (3.9, windows-latest)	9m 30s
build (3.10, ubuntu-latest)	1m 47s
build (3.10, macOS-13)	2m 36s
build (3.10, windows-latest)	12m 15s
build (3.11, ubuntu-latest)	1m 45s
build (3.11, macOS-13)	3m 2s
build (3.11, windows-latest)	9m 16s
	1h 1m 38s