I pretty much have tried the exact setup you're talking about. The ipod and the m50s work quite well. the m50s sound better without the e3 than with them (they're a great pair, and the e3 *does* improve performance with some other headphones (they do an almost miraculous job on my HD202s, but that's another story), just not the m50). To me, it tends to work ok with bass heavy/instrumental tracks, but it de-emphasises vocals to some extent.It might work better with a cmoy or a better quality amp, but for starters, you probably don't *need* one.