On a current RaspiOS both 'pip' and 'pip3' are installed by the python3-pip 
dpkg according to "dpkg -S /usr/bin/pip3 /usr/bin/pip"

I reflashed a SD to current RaspiOS and installed 5.0.0a18 via pip --user 
and also recreated the issue.   Adding the libopenjp2-7 package fixed it 
here too.

FWIW, I had an old debian_version 11.2 pi3 SD card with Pillow 8.1 that did 
work ok with the v5 software, but I previously had an old v4 setup.py 
installation there.  My 'guess' is that old Pillow version was current at 
that point in time many months ago so that's why it was there.  Regardless, 
installing v5 on the ancient SD didn't upgrade Pillow from 8.x to 9.x if 
that was what was supposed to happen.

A clean RaspiOS and clean weewx os installs and runs ok, once that 
libopenjp2-7 package is installed on a pi3.

On Tuesday, February 21, 2023 at 11:03:03 AM UTC-8 Tom Keffer wrote:
On Tue, Feb 21, 2023 at 10:55 AM Lucas Heijst <[email protected]> wrote:
Vince, I noticed on my system pip is not in directory site-packages

How did you install pip? It does not come with bullseye. If you did "sudo 
apt install python3-pip" it will go into /usr/lib/python3/dist-packages, 
not /root/.local, nor /usr/local/lib.

-tk

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