Updating HA in venv, I'm missing something here

That is correct, but to be consistent, it should look like the one described in the python virtual environment section of

After changing this, you need to run

sudo systemctl --system daemon-reload

to get systemd to notice the new configuration.
Then

sudo systemctl start [email protected]

to start home assistant
and when you are sure that is working

sudo systemctl enable [email protected]

to enable HA to start on boot.

That will get your configuration back matching most of the installations described on the website, so you should be able to do upgrades as you described in your second post.

As was said by mconway, make sure you get into the correct virtual environment before invoking pip, or will get other versions of ha installed in various places, which becomes very confusing.

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