Pip has really made management of packages in a Python installation much less frustation free, though some glitches/annoyances remain. One issue I’ve found is that it is actually a little complicated to install packages modules systemwide for all users. This is the opposite of the situation in life before Pip, where it could be incredibly painful to not have system-level privileges and use global/systemwide targets when installing packages. Definitely progress, as the the “local user ecosystem” target is definitely a more useful and more common objective.
When running “pip” to install a package from a local file system, do you get messages like “Found existing installation package_name”, “Not uninstalling package_name”, “Can’t uninstall ‘package_name’“, “No files were found to uninstall”? This could be because you are trying to install the package from within the package root directory, and “pip” is confusing the (ephemeral/coincidental) package availability from the current working directory with the package being installed and available globally.