Hi Dreamthinker, It has been a while. Welcome back! It so happens I've been playing with the 2nd gen X5 (and 2nd gen X3) for the last couple of weeks. They both sound good with the ER4S, mainly on account of the extra juice. At lower volume levels (volume matched to my iPhone 6), I'd have to say sound quality differences aren't nearly as large as I expected. For the ER4S, I'd have to recommend the X3.2 over the X5.2. The newer X3 model has a very slightly warmer sound signature (which I think fits better with the ER4S), plus it's smaller, lighter, has better battery life and still has all the other cool features that the X5.2 has (OTG USB, external DAC capability, etc.). The X3.2 does have a bit of a noise floor with more sensitive IEMs, but you'll never hear that with the impedance of the ER4S.
iTunes is a no-go. It's dragging and dropping stuff into folders. One other thing to be aware of, the EQ function on the Fiios is not very fine-grained. You get only a small number of (very wide) frequency bins to adjust. I find the Fiio EQ a bit clunky and not so useful.