I have a squeezebox radio that I use to run my "whole house" sound system. I use the headphone jack output, and then an adapter to convert stereo to mono (because I only have a single speaker in each room) and then that signal gets split. One side of the split is plugged into a small digital amp that powers a speaker in my bedroom and one in my bathroom, and then the other side of the split cable goes into a wireless transmitter (that and the prementioned amp are inside my nightstand) that sends the sound to a wireless receiver/amp in my kitchen pantry that powers a speaker in my kitchen and one in the room with my pool table. All of this is controller using the iPhone app iPeng. It is such a great setup. I just did it all about a month ago and couldn't be more pleased. See attached pictures. If you have any questions on exactly what products I used or about the installation feel free to ask. The sound quality is actually very nice, and it was pretty cheap. The speakers were $70/pair, the amp powering 2 of them was $50, and the wireless transmitter and wireless receiver/amp were about $150 for the set.
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