It appears that the Airport Express is not bit-perfect, so it wouldn't be a worthwhile investment to combine it with an expensive DAC like the DAC1. You wouldn't be getting the performance you paid for.
Whether you prefer the Apogee or the Benchmark is likely going to be a matter of which flavor you prefer. You can get a fairly good idea of the sound of the Benchmark by reading the Stereophile reviews as well as Iron_Dreamer's comments here. The consensus seems to be that the highs and midrange are very sweet, and the overall sound is very fast, but the bass is not as prominent as with some other DACs. (Incidentally, this pretty much matches my impressions of the sonic flavor of the Analog Devices DAC used in the Benchmark.) Fewer Head-Fiers own the Apogee unit so it may be harder to get a handle on its sonic flavor. You may also want to consider the Bel Canto DAC2, which uses the same ASRC as the Benchmark and thus probably also has strong jitter immunity (this is important with computer transports), but uses a different DAC chip. There are a variety of reviews of the Bel Canto around here on Head-Fi, and there is a Stereophile review.