According to the T&Cs you won't earn miles for these purchases. In reality, generally you will (but this could change at any time). You even earn miles for AMEX gift cards purchases directly from AMEX, so it's not an issue of "they can't tell what you bought at staples" (although that is true) but more an issue of an unenforced rule.

I don't know what charge smart is so I can't speak to the second part of the plan.