It seems to me that whenever I start a shuffle on my phone and transfer to play on another device (my computer) via Spotify Connect, the same 20-30 songs are shuffled but not the entire playlist. It happens to when I shuffle a playlist folder and when I shuffle a playlist itself. When I shuffle the playlist folder, it chooses a random song that starts with A or a # and the rest of the songs fall in that same category. For playlists, it shuffles the first 30 or so songs that are on the top of the playlist.
I'm not sure if this is the right forum for this because I don't think there's a solution to this but rather I would like to bring this up to Spotify's attention as this seems to be bug.
1. Start shuffle of a playlist or playlist folder on phone (or possibly any device)
2. Use Spotify Connect to transfer sound to another device (for me it was PC)
3. You will notice the shuffle will no longer be a true random shuffle but very predictable
The workaround for this is if I start a shuffle on my computer and then control it from another device then the shuffle works fine. It's when you start a shuffle on one device THEN transfer sound via Spotify Connect is where the shuffle goes bad.