Not exactly the same design as the Westone/Shure type shells, which have the cable over the earlobe to take some of the strain off the ear canals gripping the bore through the eartips.
Other semi-custom designs spread out more of the weight and friction all over the outer ear.
Not to mention you need to try other tips. I have the Aurisonics above but I use it with the Sony Hybrid - soft flange with a thick but soft core.
I have the ASG-1.3 - smaller than a headphone, fits into a water-proof case, doesn't need to be charged unlike wireless headphones, easily driven by a smartphone, etc.
You don't really have that much of a choice, the X1II is the only one at that price range (excluding the iPod Touch) that has BT for wireless headphones.
Also, as far as the wireless headphones are concerned, the DAP's other circuits will
not matter at all, since it transmits digital and will be decoded by the circuit built into the headphone.