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Lots of questions.... Maybe this will help with a bit.
1) Either. You can use either Photoshop or Illustrator to create any basic image. It's only a matter of preference. Most sprites end up in raster format so even if you use Illustrator you can save to a raster format. If you need vector sprites, then obviously, you must use Illustrator.
2) There are a couple of ways.... If you are using Illustrator's Live Trace, have you then tried Illustrator's Live Paint? That's what it was designed for. You can also select objects and simply fill them with color. If you want to use Photoshop, simply place your outline on it's own layer and change the layer's blend mode to "Multiply" then add a layer BELOW the outline layer and paint on that layer. This will keep your outline on top and looking clean.
3) You need to adjust the Live Trace Options. You can do this by selecting the raster image and choosing Object > Live Trace > Tracing options. Play with the settings until you get something you do like.
4) When you reduce in Photoshop, try setting the interpolation option to "Nearest Neighbor" this may help keep your lines crisper.
5) Painting is a matter of study and practice. You need to pay attention to how light and shadow works against different surfaces and try and mimic that. The more you practice the better you will get. There aren't any real shortcuts.
Hope that helps
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