What's the problem this feature will solve?
Tools could use simple lookup logic for checking their latest and stable versions. The way it is currently done in pip is crazy:
https://github.com/pypa/pip/blob/35d51f1f405f6f31d68c800e73307686ec029254/src/pip/_internal/utils/outdated.py#L104-L118
Describe the solution you'd like
It should be as simple as fetching https://pypi.org/pypi/pip/latest/json or https://pypi.org/pypi/pip/stable/json endpoints.