Hi Ben, have given this a try... I was hoping to put in a rule that does something with the Squeezebox binding ever 15 minutes, thus waking it up if it's not properly connected.
About the most unobtrusive thing I could see whas maybe adjusting the volume down by 1% and then back up by 1% but this doesn't seem to force a reconnect. If I update the "play" to off and then back on then it properly re-establishes the connect. But if I did this every 15 minute's I'd be sure to get some complaints from the rest of the family :-)
Will keep an eye out and hopefully you get your dev environment back up and running some time.
Thanks again!