dang this is a really thorough list of ideas and design in your document so far! also i loooove the personality in your concepts already so far. it might be helpful to flip them so viewers don't have to turn their heads sideways to read the labels haha--i think if you upload to imgur it gives you some basic image editing options like rotation.
the trello looks great so far! i'm intrigued by the "primary quest" vs "secondary quest" labeling. i'm guessing this is a priority labeling? it's a cute naming convention haha. i had a quick suggestion for the board: i think it could be really helpful to think of your priorities in 3 tiers--something like high, mid, low, and the colors red, yellow, green which are really easy to read and understand at a glance (and the way trello organizes labels, red, yellow and green will actually show up /before/ the other colors--which makes appear first on all cards and even easier to read down a list).
