Here’s a HOW TO on copying a CD (with live material, for example) to a single AAC file w/ embedded Track info for duplication with iTunes or listening truely gapless on a modern iPod. iTunes 4.9 introduced “Enhanced Podcasting Technology”. iTunes also has “Audiobook Technology”. This technique involves combining the two. Your resulting file will benefit from both. For example, images could be placed in the file (covered elsewhere) that change as the tracks/chapters do (like enhanced podcasts), and listening position is stored (like an audiobook). Link.
HOW TO make gapless CDs