Upgrade all --user installed pip packages and solve basic dependency conflicts. Use at your own risk.

pip_upgrade_all.py

#!/usr/bin/env python
from subprocess import call, check_call, check_output, PIPE, Popen


def main():
    packages = check_output(
        'pip freeze --user | awk \'{gsub("=.*","",$1);print}\'', shell=True, text=True
    ).split()

    check_call(f"pip install --user --upgrade {' '.join(packages)}", shell=True)

    print("")
    print("-----------------------------")
    print("| checking for conflicts... |")
    print("-----------------------------")

    call(["pip", "check"])
    proc = Popen(["pip", "check"], stdout=PIPE, text=True)
    conflicts = proc.stdout.read().split()

    if len(conflicts) > 0:

        print("")
        print("------------------------------")
        print("| solving basic conflicts... |")
        print("------------------------------")

        for conflict in conflicts:
            chars = ["<", ">", "="]
            if any(char in chars for char in conflict):
                conflict_version_string = conflict.replace(",", "")
                check_call(["pip", "install", "--user", conflict_version_string])

        print("")
        print("-----------------------------------")
        print("| checking remaining conflicts... |")
        print("-----------------------------------")
        call(["pip", "check"])


if __name__ == "__main__":
    main()