One big deal is OS compatibility. As an example, the AK series is terrible to connect to Mac OSX, whereas the ZX2 is just fine.
I have both the AK240 and the ZX2. In my opinion, the SQ is very good on both of them. I have not used either of them with an amp because I just don't think it is necessary. I bought the ZX2 mainly based on its ability to stream from Tidal, but have been very satisfied with it as a DAP once I worked around a couple of UI issues with playlists. I also have an iPhone 6 with an itunes library on it. I have an Oppo HA-2 amp that I use with it. My current IEM of choice is the Shure 846. I would recommend the ZX2 with the 846's, OR the AK100 II with the 846's. Both sound very good and if you use a 200GB SD card, have about twice the capacity of the largest memory iPhone. Using a balanced cable with the AK100 II or a TRRS cable with the ZX2 works great with the 846's. The line out on the AK100 II works very good with an amp. I would say that the SQ of the AK100 II is as good as the AK240. The only major difference beyond capacity between the AKs is that the AK240 has duel DACs while the AK100 II is a single DAC. I didn't notice a perceptible difference. Just my opinion based on my tastes.
Thanks. That's very helpful. I confess I haven't even started thinking about different cable options. Do they really make much difference?