I am interested in revamping the ToonTask template. And yes, I think "playground" looks much nicer. The part with the description is the type of task (visit, assist, defeat, and so on) and should be in the Minnie typeface (one of the typefaces used in the actual game.
As for that last question...I'm feeling indecisive. I'm not sure which one would look better.
I'd probably have to show you to explain some of the details.