Firstly, I'm guessing you'd want to avoid that music "enhancer". I doubt it would actually improve the sound, because as far as I can tell, it would probably just colorize the sound. But I haven't actually gone out of my way to figure out what exactly it would do.
Your most practical choice would be to use an HTPC. Lossless storage is quite practical if you're using a computer, simply because 3.5" hard drives are very cheap, as opposed to the 1.6" or whatever they are in iPods.
Also, it might be preferable to interface with an HTPC instead of an iPod, because with the iPod you are required to use the DAC built into the iPod. If you were to connect your HTPC to your reciever via a Toslink cable, you wouldn't have ground loop/noise issues, and you'd be sending a purely digital signal to the reciever for it to decode. The nice thing here, too, is that there are many motherboards with onboard optical out, and you can many cheap soundcards with an optical out. Whereas the analog sound coming out of onboard sound, as well a cheap soundcard, is not so stunning, if you leave it in a digital format, you don't get those drawbacks.
In general terms, I don't see the iPod as being a viable source for discerning audio playback. It simply has too many technical drawbacks that hold it back in terms of sound quality. It's built for portability, not so much for great sound.