How do we register custom plugin with LMS the correct way?

See Settings/Information for the various Plugins folders where you can put your own plugin. Please not it must be Plugins (uppercase first character, "s" at the end), and NOT the folder inside the cache.

On RPi / Debian I saved MyCustomConvert plugin in

/var/lib/squeezeboxserver/cache/InstalledPlugins/Plugins/MyCustomConvert

Not this one :-). It's managed by the built-in plugin manager.

 From web interface 'Settings>Advanced>File types' I could now see my
changes but now I got a message that the server had to restart to use
the new settings. This before I've done any changes from Web GUI. *After
restart from the web interface I now find my MyCustomConvert directory
have been deleted.*

Exactly. Don't mess with the plugins folders inside the cache folder. There are others you should use.

Finaly I ended up copying 'MyCustomConvert' to
     /var/lib/squeezeboxserver/Plugins

That's the one to use.

Are we to understand the '~/InstalledPlugins/Plugins/' directory are
protected/maintained and ment only for official plugins?

Not the official ones, but those installed by the Plugin manager in LMS. Those you select from a list and then are downloaded and installed automatically.

Will content in '/var/lib/squeezeboxserver/Plugins' survive an LMS
upgrade?

Yes.

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