suns2 wrote:
I have clicked both flip board icons multiple times, and toggled on/off "White always on Bottom" . I have toggled every other setting i can find.
I could be wrong but I think it has always been that way. I don't use the feature that often, so the odds of being wrong is high 
If you have seen it match the board in the game, or for the color of the player in in the past, you can bug report it under Help > Report a Bug or open a ticket. Or use Make a Suggestion.
The analysis line, such as the book move in your screenshot, does show based on the orientation of the board.
I have clicked both flip board icons multiple times, and toggled on/off "White always on Bottom" . I have toggled every other setting i can find.