AirPlay / Airport Express and Square magstripe reader compatability?

[parable]

I've run into a problem in my cafe, trying to stream music via AirPlay to an Airport Express and at the same time trying to use my Square reader—both from the same iPad. The Square Magstripe Reader won't read cards if the music is playing, unless I unplug and plug it back in, which then makes the iPad think I'm plugging in headphones, and it stops streaming to the Airport Express.

Has anyone else encountered this problem? Found a workaround?

[VanKalkerFarms]

The square reader that plugs in uses the same audio interface as headphones so you will not be able to use that iPad to stream music and accept payments. 

Also  as a different problem you should make sure you have license/permission to just stream  music publicly in a store. Places like pandora and others have business level plans that are like $25 a month.