Improve Update Workflow testing UX #2305

Job	Run time
build-and-test (ubuntu-latest, oldstable)	17m 7s
cloud-test	0s
build-and-test (ubuntu-latest, stable)	25m 38s
build-and-test (macos-intel, oldstable)	18m 24s
build-and-test (macos-intel, stable)	18m 37s
build-and-test (macos-arm, oldstable)	17m 29s
build-and-test (macos-arm, stable)	17m 19s
build-and-test (windows-latest, oldstable)	21m 0s
build-and-test (windows-latest, stable)	22m 4s
features-test / test	1m 58s
	2h 39m 36s

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