I'm using an Apple TV 2 hooked up to a Denon 4308 receiver and Bower & Wilkins 683 speakers.
Nice system you have there. Here is some thoughts but not answers per se -
In general I can tell the difference between mp3 and aac files both at 256. A well done mp3 file at 320 can be extremely good as well.
I have a particular LP that I later got as a CD and also downloaded it from iTunes. There is a definite difference in how the 256 AAC file sounds compared to the CD. The LP to me sounds best but the CD is pretty darn close.
My problem with iTunes is that we don't know what the "Masters" are. This is not much difference between when we get a DVD that just sucks beyond belief in quality of transfer and those that are done by a good master with some craft. My point is that not everything on iTunes is great but some are very good and worthy.
If you want to do matching from iTunes, be sure you know what you are getting best you can. If you already downloaded a song from an album and like the quality then chances are the rest of the album via match would be to your liking. The biggest loser downloads are any recordings that are vintage by nature. Newer recordings tend to sound very good from iTunes.
I did a test where I played Carole King's "Tapestry" album via LP, then CD and later my friend's 256 AAC files. Last, I downloaded from HDtracks higher res flac file version. Here is the order of preference that we liked -
Best - Flac 96/24
LP
CD
AAC
Later, we did a lossless Apple file from the CD and it was just slightly better sounding than the AAC 256. One had to listen carefully. - Remember, this is all subjective and limited to equipment.
My equipment included a Marantz AVR, Oppo103, NAS storage, Mac Mini, Audacity software, Pioneer Turntable (upgraded), Garage custom turntable, vintage but spectacular Dynco PreAmp for both turntables, Seinnhauser cans, and older but moderately faithful Energy speakers. Between all this we have what might be a music hobbyist set up but certainly not audiophile level. If we can tell on this system, chances are you might too.