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I'd like to note from the start that this is a deal breaker for me.
When playing on my phone or my PC, shuffle works perfectly. When I decide to switch to my Google Home, my now playing list changes. It selects about 20 songs around the currently playing songs and shuffles those on repeat.
If I use the "shuffle play" option from my playlist instead, it will choose about 20 songs from the beginning of the playlist. (Mind you I have a little over 2000 songs in my All Songs list). I tested this by sorting my playlist by Title, then hitting Shuffle Play. There are two results of this exact method posted as screenshots. One connected to Google Home, one not connected. You'll note that the Home connected screenshot only shows songs that begin with numbers or the Letter A.
This has been reported on the forums, but never officially in the bug reports. See below. It appears to be all cast devices, not just Google Home(PS4, Chromecast, etc). Also occurs across Android and iPhone.