I think you pretty much summed it up the Wadia and ?. I don't know of any other product that can pull digital out of the ipod short of a few companies that have to mod the actual ipod to get it to work and costs way more. The Wadia is a great product and sounds great too. It doesn't work so well with older ipods or even the iphone. I think that is the main reason you see so many for sale. It is a little misleading that they support older ipods. I have a 5th (I think) generation ipod 80GB that they only way it works is you have to start it playing and then dock it and it will continue playing with the screen basically blank (you can't see what is playing) The iphone sort of works but mine constantly keeps beeping and asking if I want to turn on airplane mode to avoid interference. I just picked up a new ipod classic and it works perfect. If I were only going to have an older ipod to use with it though I'd sell mine for sure.
Also if your son is not ripping to at least lossless then you may want to reconsider everything since that is the most unmusical experience possible. That is listening to digital music via MP3 quality.
Also if your son is not ripping to at least lossless then you may want to reconsider everything since that is the most unmusical experience possible. That is listening to digital music via MP3 quality.