I'm not sure why you're worried about awkwardness when you're willing to carry an amp with a Sansa Clip, but you could always get a right-angle plug.
I am planning to get the Sansa Clip+ and pair it with iBasso D2+ boa as my portable rig set up. But i cant help but notice the headphone jack of the Clip+ is actually at the side, not top nor bottom. If i plug in a mini-mini interconnect between the Clip+ and the D2+ boa, wont the cable be in a very awkward position? I mean, comparing to fuze where it heaphone jack is at the bottom. If any one of you have similar set up, mind to post a couple of photos here?