Nick, sorry to hear about all the headaches you've had. I've been using various squeezeboxen since about 2007 as well and there were many times along the way I was ready to give up on it for similar reasons as yours. But what I have now works soooo well. The real test is that my wife can crank up tunes in the kitchen via ipeng on her iphone or ipad and it all just works. While it all works extremely well for me & my family, I doubt I would recommend it to anyone at this time for obvious reasons... its future is unknown and sooner or later support may stop. Like Sonos, Auralic and others, new solutions are bound to arrive that will ultimately be better, more intuitive, more stable than the Squeezebox technology.
But damn, Slimdevices was so far ahead ahead of its time. The first product, SliMP3, was released on 2001. The SB2 in the spring of 2005 and SB3 just 6 months later. But then along came Logitech in 2006. Sadly, they never really understood how to market and support these products and ultimately gave up on it the summer of 2012. It has actually been quite amazing to see the continued community support over the last 2 years. Prices on a used Touch on ebay still exceeds the original pricing. I think many fans had high confidence in the Community Squeeze effort - but who knows if that will continue through product.