This isn't really an 'audiophile' answer, but I think a critical question is how do you want to control your secondary/outdoor SB? With an airport express you'll either have to (a) run back in the house to select/skip/etc. tracks, or (b) control the SB inside via PDA or similar networked remote. My guess is you'll be much happier with another SB, simply from a convenience standpoint. And the bonus is that people at poolside don't have to listen to the same tunes as the people inside.
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