I'll happily +1 the recommendation on the E11. I've had mine for about a week, and already very impressed. Very light, about the same footprint as a credit card (and as thick as a deck of cards, I guess), and gives a good shot of mustard to your DAP. Very noticeable difference, especially with better headphones (ie with my earbuds, I can pick up that there is a difference, but with my M50s, it's night and day). For just under a hundred bucks (that's with tax, shipping, and extra cables), I'm very pleased with it as an entry-level portable amp, and I can't imagine much out there that gives you better bang for your buck.
Player-wise, I'm currently using a iPod Touch as my pocket player, though I'm strongly eyeing some of Cowon's offerings such as the J3 as a way to go the FLAC route (currently, I have to use my EEEPad if I want to bring FLAC with me) and get away from Apple products. I believe the Cowons are held in fairly high regard for the sound quality they offer, so one of their players may be worth checking out.