Re: Subdividing and Smoothing
It's probably something with your topology; I'm guessing that front face is all one poly. How you layout your surfaces and the direction they flow can radically affect how they are smoothed when subdivision is applied.
The easiest rule of thumb to make subdivisions work well is to stick to quads (four-sided polys) for all of your surfaces. It's not a requirement--other shapes can be smoothed with planning--but if you stick to quads you can be pretty brain-dead about your layout and it will still work. Remember, the way subdivision surfaces work is that the surface is split in half on each axis and averaged. Since a quad is already four-sided and will therefore split evenly, it's very hard to go wrong.
If I were going to lay out the topology for your shape, I'd do it something like this:
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