Well, there is always the option of doing what I have done lately - build up a small collection of DAP:s. I use them all and I like the variation in sound signature they offer. I have one with progressive metal, one with thrash/speed metal, one with progressive rock, one with pop/rock etc. The it is more a question of "which type of music do I feel like listening to today?".
If you are looking for the DAP to beat them all you will always chase after rainbows since newer and better ones will always come out.
Anyway, I do not know if we are contributing anything to the OP:s original request for good sounding DAP recommendations. Considering his current gear, a Clip (+) would be a good upgrade (even if I do not own one, I recommend it). Earphone wise, if the OP likes earbuds, I would recommend Yuin PK3. If he likes smaller portable headphones, the Portapro might be good (however I prefer Sennheiser PX100 to Portapro - the PX100 are more laidback and less aggressive, but a bit more detailed and "airy" than the Portapro, something I like).
By the way, DrBenway, I love your signature. I love the Marx brothers! "I feel like joining a club and beating you over the head with it!"
Edited by Danneq - 5/16/10 at 12:59am