I made the decorations out of fondant, as you can probably tell. There are TONS of tutorials online for making owls of all different styles. I just kind of looked at them and decided to wing it (get it? wing it! ha!) The owl's body was made with an oval cutter and then I took another round cutter to take a piece out of the top to make the ears. The wings were originally half circles but they were too big so I cut them down to kind of a tear drop shape. Everything else was pretty easy. I used the end of a frosting tip to make the circles for the eyes and also used it to make the "feather" impressions on the body.
The diplomas were pretty simple. I just cut out strips of fondant and rolled them up! Then I cut out a litte strip of gray fondant for the "ribbon", put a dab of water on the diploma to make it stick, and wrapped it around.
The best way I've found to transport a large quantity of cupcakes? Plastic storage bins with snap-on lids. They leave plenty of head room for the cupcakes so you don't smoosh your frosting or decorations. They also can be stacked and are pretty sturdy (sturdier than cupcake boxes and ESPECIALLY the pieces of garbage they sell at Michaels). Also - reusable!