core.py: Make error messages more verbose (#2453) #1723

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Job	Run time
typing	19s
3.13	23s
3.12	18s
Windows	41s
Mac	15s
3.11	23s
3.10	21s
3.9	27s
3.8	25s
3.7	16s
PyPy	31s
	4m 19s