Using the Earsonics SM3, I have a 5.5G ipod and finally, the headphone jack broke (seems to be a common problem but mine lasted quite a few years with heavy use). I love the high capacity of the ipod, and believe me, I use it because I never know what mood I'll be in an hour after I walk out my door. Until my decision is made, I have a Clip+ to hold me off but it's small (capacity-wise) so it's going to be temporary. Maybe even use my iphone 4. I could just go for the amp since that would bypass the headphone jack anyway. But I use the SM3, and everywhere I read, an amp is completely unnecessary for it and if I choose the wrong one, would even make it sound worse. I could buy a new DAP. Really, though the only one that seems like a real upgrade is the Cowon X7 because of its capacity and even better SQ but it sounds like Cowon did what I needed right with it and then decided to go backwards with a lot of things (stability issues, especially for Mac OSX users). Everything else just tries to sell frills and I have my iphone 4 for that kind of stuff. I'd just sell my iPod as-is to someone who'd amp it and my super.fi 5 pro to help fund whatever I'll buy, but I feel like it'll be a parallel trade-off rather than an upgrade since it sounds like anything else high-capacity is lower in SQ (Archos 5) and anything else high-SQ is nearly less than half in capacity. I could repair the headphone jack. Cheaper than the other options, but I don't know any opinions on the ipod/SM3 combo. I could rockbox it, but to be honest, I can't figure out how to make a playlist where I can define the order of the songs I want manually from different albums. So that's my conundrum. If I didn't have the SM3, the decision would've been easy, I bet (There's this part of me that's telling me to go the amp route; that'd be the home-audio rig side that I'm more into) but doing that may not be worth it.