Hi- yes wireless can potentially always be an issue - very prone to interference and not much can be done about it. A wired approach will always be more robust.
For me a $2,500 iPod misses the point of what's going on in the marketplace. First, a totally tricked out Squeezebox is a lot less and does a lot more.
But more importantly - at least to me - is that the whole PC thing is all about using widely available, mass market, highly standardized products to drive prices down without compromising quality. Put another way, when a 500Gb hard drive is $139 an iPod for $2,500 is nuts.