Thank you for opening up those parts of DFWs life to us. To me, you've well established DFW believed he cycled between performing and depressive selves and that he preferred seeing each of them from the perspective of the other self -- a masochistic and profoundly undetached introspection. You've also well-established that DFW saw a release from that cycling in trying to vicariously think like selves other than his, i.e., "typical" selves in trouble as described by the self-help books. Unfortunately that also led to DFW's reliance on mirroring external views about him uncritically, perhaps as a buffer so he could mediate the efforts of well-meaning helpmeets. DFW also seems someone especially burdened by his self-perception of what Harold Bloom called anxiety of influence. It seems like he had problems distinguishing a systemic decomposition of influences from drowning in influences. But (speculatively) I think the overarching issue was that his internal critic was masochistic. If you don't aim to win, you're not going to fully work out or execute a best strategy. You'll set yourself up to lose. I wonder if DFW ever wrote about management consultants, because often they get paid extra to "do the hard decisions" and "take the blame."
Where I guess I part the ways is in your speculating about his mother. You report lots of evidence of DFW's manipulating and delighting his teachers. I doubt that was to please his mother. She and he both seem to have had monstrous charismatic talents. And he clearly had great guilt about it. What that has to do with Alice Miller eludes me, but her books have a way of taking credit away from kids and reassigning it to parents, and that sleight of hand displacement of blame seems a very American meme. Don't blame Eichmann, blame his mom. Then we'll understand.
I'm glad you brought this to us. DFW was an exceptional person. Thanks.