Thanks for your thoughts. I like the Stello DA100 a lot, and consider it a great "bang for the buck". For the Neko D100 to sound similar is not a bad thing, IMHO.
I was thinking that maybe you could spend more time over the next week listening to complete performances with one DAC at a time; as differences in musicality, presentation, detail and transparency sometimes become more obvious as you become more or less involved/immersed in the performance. Especially when the timbre/tone or frequency response are so similar.
And, using "less than lossless" source files means that both could be performing below their limititations, and therefore you may not hear the advantages one DAC has to offer over the other. I know some of your files are FLAC, but others are not, and I would stick with lossless only, or CD or whatever is the highest quality recordings you can get. Only then can you hear all the detail with one DAC that the other might miss, and so forth.