Excellent write-up although some of it makes for politically painful reading. Since about mid-2017 I've felt that DSA's problem isn’t structural but cultural which means they are even more difficult to change, fix, and root-out because the same problems that exist now would manifest themselves anew in new forms even if the organization were radically or perfectly restructured. And DSA's cultural problems—bullying, the weaponization of procedure (especially grievance resolution mechanisms) class reductionism, racism, sexism—are rooted in DSA's material basis: The big-city middle (and even upper) class types that constitute its core membership base and dominant leadership layers. These people are disproportionately white in places where the working class is either majority or plurality people of color and so the organization's whiteness problem or "Bernie bro" character sticks out like a sore thumb to almost anyone who isn't a middle-class white person. A Black LGBTQ working-class revolutionary I've known for decades was super-enthusiastic about DSA's growth in 2017 until he went to a local DSA meeting and encountered nothing but "grad school jargon" (to paraphrase him) and the organization was basically dead to him from that point onward, not because he was abused or because somebody said something (inadvertantly) racist in the meeting but because working-class people simply do not have the time and energy to respond to—let alone fight and fix—all the BS that goes on in these hostile social environments. Life is too short for that and there are bigger, more important, and actually winnable battles out there in the world to fight which means fights to control of DSA are increasingly going to be won by the organization's most insufferable elements through a process of natural selection, a revolving door grind that repeatedly weeds out the sensible, the principled, the dedicated, and the pragmatic who also tend to be working class and/or people of color i.e. groups that face real, serious problems in their daily lives that can only be overcome through successful real-world organization and struggle.
Perhaps the best thing that can happen given the above is for DSA to serve as the beginning rather than the end of people's activist lives and careers. Most of the tens of thousands of young radicals who joined SDS in the 1960s gave up on changing the world entirely when they stopped being active in SDS and it would be a real shame, a colossal waste, and a historic setback for the American left if that ends up being true of the people who join and then quit DSA. So far, it seems like people who are giving up on DSA aren't giving up on the struggle and we should do everything possible to strengthen that trend.
Which is a very long-winded way of saying I hope you keep reflecting, writing, and sharing your experiences about what works and what doesn’t because it’s invaluable and helps other people learn what to do and what not to do in their own organizing.