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Hi Elluminatus,
Thanks for the clear and detailed questions. Here goes:
1. We have not tested the XSqueeze plugin, especially not under the C2. However, according to the documentation, it should work fine. You could test it out first by checking whether a Squeezebox Server recognizes the Kodi-Player from XSqueeze in its web interface.
2. Max2Play only needs to run on the Pi’s you want to use. One of them should have the Squeezebox Server installed and all should have Squeezelite running. If you want to use your dataserver’s music, you can mount it on the Pi with the Squeezebox Server to access all your music from anywhere in your network and play it to all Squeezelite players.
I hope this clears everything up. Check our Multiroom Audio Configurator to find the right setups for each of your rooms: https://www.max2play.com/en/multiroom-audio-configurator/