Improve assertions in test for python upgrade script #4144

Job	Run time
Build wheel and source distribution	33s
aarch64-unknown-linux-gnu (ubuntu-22.04)	3m 46s
x86_64-unknown-linux-gnu (ubuntu-22.04)	3m 21s
x86_64-unknown-linux-musl (ubuntu-22.04)	3m 54s
powerpc64le-unknown-linux-gnu (ubuntu-22.04)	3m 47s
x86_64-pc-windows-msvc (windows-2022)	8m 0s
i686-pc-windows-msvc (windows-2022)	7m 16s
aarch64-apple-darwin (macos-12)	9m 32s
x86_64-apple-darwin (macos-12)	8m 24s
Build macOS installer and sign/notarize artifacts	1m 3s
Build Windows installers	1m 7s
Publish release	0s
	50m 43s

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