Improve Update Workflow testing UX #2292

Job	Run time
build-and-test (ubuntu-latest, oldstable)	9m 44s
build-and-test (ubuntu-latest, stable)	25m 41s
build-and-test (macos-intel, oldstable)	17m 51s
cloud-test	0s
build-and-test (macos-intel, stable)	19m 10s
build-and-test (macos-arm, oldstable)	17m 19s
build-and-test (macos-arm, stable)	18m 15s
build-and-test (windows-latest, oldstable)	21m 35s
build-and-test (windows-latest, stable)	20m 52s
features-test / test	2m 21s
	2h 32m 48s

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