From here I will have to wait at least a few weeks for the LM386 amplifier to come in the mail (I ordered two from different stores, lets see who wins the race...). I am still having thoughts about what to do with the switch, I could use it to enable streaming audio.
I have also considered making it power up from the switch, making the SD card read-only (overlay filesystem) and automatically start streaming whenever the pi boots up.
I haven't looked into what software there is to drive the speaker from my phone, if anyone has a suggestion, drop a note in below. (VLC remote?)
For now, as a bedside speaker this should work fine with quiet audio.
Nothing is glued or stuck down, I also intend on addressing that in the final design as well.