>I mean the thing is, his live set is essentially about four
>"tracks" woven together, and he writes a new show for every
>show. But these tracks are generally 8-20 minutes long, and
>have all these sweet ideas trapped inside of them that, from
>what I can tell at his shows, makes for a dissonant listen
>except for geeks like me and him.

Nothing wrong playing for geeks and making challenging music, but, he just needs to keep in mind that music of that kind many times tends not to translate to a huge commercial following. It CAN, but, it can be a task. But, if it has been accomplished before, it can be accomplished again.

>So all I've ever said is, maybe let people digest those pieces
>individually, and in the process maybe you can find the
>personality you truly find inspiring. I bought him a Lou Rawls
>LP from Goodwill, All Things in Time, and he samples from it
>almost religiously. Yet at the same time his main set is very
>Animal Collective.Daniel Lopatin inspired.

That's definitely an option. That would really help if he intends to release a single. Also, maybe getting some other producers to remix his output might help to give it unique feel that he might not have even envisioned himself.

I can say that I listen to some stuff that leaves the casual music listener with a grimace in their face, stuff like Autechre, Squarepusher, ECM free jazz, etc..., and I enjoy the challenge they can be, not knowing what will follow, rather than my typical habit of knowing what chord/note will follow in popular music.

Your boy sounds like he's pretty dedicated to his craft (anyone that does an entirely new set for every show definitely is), has some pretty great musical templates to emulate (Maflib) and sounds as if just needs to refine and focus at this point.