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Is there any way to install system-wide the asked Microsoft Fonts, instead of downloading each user on first startup?

Thanks.

Open /usr/share/playonlinux/python/lib/Variables.py

Replace the following line

os.environ["DEBIAN_PACKAGE"] = "FALSE"

with

os.environ["DEBIAN_PACKAGE"] = "TRUE"

PlayOnLinux will behave like the version installed in the debian package. Be careful, some other change will occur

Will the Variables.py file be replaced on each package upgrade?

I see that there is commented:
# Debian packagers should switch this to TRUE

If Debian packagers aren't setting that variable properly, a solution could be to detect a Debian environment (for example, by the presence of the directory /etc/apt)

Thanks.

But I'm thinking now: I'm using packages from deb.playonlinux.com !

No, that's not the problem. The .deb provided by debian packagers use system fonts while we prefer to downlad them from Microsoft website (it's more portable). So if you set this switch, your playonlinux install will behave like debian one. (You need to change this switch each upgrade)

Are packages in deb.playonlinux.com made by you?
In that case, could you package those with the switch already changed?

Thanks.

The debian switch is really specific, and our package is not made to have it enabled by default at all. (For example, PlayOnLinux won't be able to find locales anymore, so it will be in english).

A solution could be to detect that POL is in a Debian environment (for example, by the presence of the directory /etc/apt), and with this test set the default value for os.environ["DEBIAN_PACKAGE"]

Nope, it is not an environement problem. It is the way the package is organised.