Nice job! A few things that would drive me crazy as an animator: Pirate on the right: That floral pattern! OH GOD. At least in Flash (maybe Toonboom) I could mask that, and the skull/crossbones. Traditionally, I'd be begging for that pattern to be taken off.
Little pirate in center: Not bad, end of beard is a bit overly complex. The brim of his pirate cap doesn't need that extra line.
Pirate on the left: Much easier. Looking a those feathers on her hat. Animating in Flash/Toonboom should be fine with a symbol.
This concept may help. Try drawing the same character multiple times, and after a few times you'll realize what the most tedious parts to redraw are. If you want to get really fancy, line up those drawings afterwards and have them on a loop in a .gif (esp. if in the same pose) and see which parts warp the most. I'd recommend a really low frame rate (like 3-6 frames per second) for a non-animator. Many programs make certain details easy to re-use without much boiling or going off-model. Like using masks in Flash, or just symbolizing details. But traditionally, you have to redraw every details for every action, at 12 drawings a second normally. But yeah, you really don't know until you've animated with them.
Could be either really, the design of a compass can include a little disc that flips up which could also be a pearl in this case since the image is a little ambigious, the colour and material the thing he is holding is made out of isn't known and the shape could be stylised or an ornate design.
Heck, I'm sure someone out there has made a fancy compass that resembles a clam.