From my experience the most significant issue DSA faces is that they're incredibly fragmented and disunited. They function more like a loose network of activists who come and go than a political party. Members are allowed more or less to believe and act how they want even if it's unhelpful or harmful to the organization. This manifests in their most prominent members blatantly contradicting the organization's positions, but it also manifests in basic administrative tasks not being completed and a disinterest in building a robust internal culture, camaraderie, and pursuing democraticly decided political goals. They might be able to unite around a (usually local) issue but once that matter is settled or the energy dies down then most people drift away until new wave of activists joins up for something else. It also allows for scattered campaigns as people try to pursue their own interests within the DSA only to not have the organization materially support them because nobody else actually wants to do the thing.

If that's reflective of your experience then I would suggest trying to build a culture of party loyalty, discipline, and focus. Idk how to do that specifically but it probably involves mandatory political education.

There are a lot of things I could say about DSA pitfalls and organizing generally but I'll try to keep it short.

1. Do constant internal political education so that you can adopt lines and move towards one another rather than establishing (often reactionary) factions. DSA develops reactionary factions like it's their only reason for existence. Incorporate it into the new member onboarding you mention.

2. Establish a culture of strategic organizing, not just organizing to do things or even to achieve the overt goals of praxis. A sign of a healthy org is one in which a working group is doing actions in order to, for example, gain an embedding in a community, gain stronger understanding of conditions, and build membership rather than only considering the direct value of the action (show support for Palestine, support BLM, stand strong with unionizing workers, etc). DSA and other orgs seem to mostly do this accidentally, miming historical praxis and reaping some benefits, but because they're not cognizant of what they're doing they miss opportunities or gain an unrealistic idea of what successful organizing looks like. As an example, the DSA tendency to overinvest in electoral work to the point that they don't even do a good job at it - they just knee-jerk do it like it's a compulsion. A key element to avoid this is to do constructive criticism sessions after actions, where you invite critique of what could be done better next time and how you're measuring success.

3. Be part of coalitions, especially with communities you want to embed within. Once you are a reliable partner you can suggest directions without alienating the coalition. This is a good way to, for example, develop an anti-cop position in a coalition.

4. Be vigilant against dogmatic factions by exhausting them before they exhaust you. You must alienate people who currently have no capacity to adopt correct positions through dialog or education. This probably sounds toxic in itself, but it's a reality of combatting reactionary tendencies in the imperial core. The inverse happens constantly: a toxic group or individual makes a space exhausting for the rest of membership and they decide to bail on your org. Example: make no space for transphobes, pro-cop positions, or chauvinist positions. You need to police the bounds of acceptable discourse or you'll make a space that is inhospitable to the people you actually want in your org. DSA is primarily characterized by factions alienating each other and new members.

5. Authentically embed in community. DSA chapters are often poorly regarded among black orgs in the South because they try to do their own thing without understanding community needs and community safety. There's a stereotype of DSA white dudes putting others at risk through poor organizing skills, a lack of care for safety, and escalating at actions, for example. There is almost certainly a vast and precious resource of experienced organizers and community members for you to tap into if you start from the position that you have things to learn from your communities.

6. Socialize frequently and with the whole chapter. Many potential conflicts within an org can be resolved through simply chatting at a social event. Ensure that social events are safe and that people feel comfortable at them. Check in with people regularly, especially new members.

7. Be ready for conflicts. As your org grows there will be grievances. Handle them rapidly and fairly and with attention to justice for those harmed. Develop contacts with independent mediators right now. "Justice delayed is justice denied" applies to DSA chapters and they're notorious for trying to sweep things under the rug for the sake of "unity" or because they're buddies with people that caused harm.

You need an exit strategy. DSA cannot ever be the vehicle for socialism, so you need to be aiming towards another vehicle. DSA is a big tent, it is ideologically broad. This will cause conflict the minute someone with the will to power comes in. You should start establishing hard ideological lines and ways to mediate when people cross them.

You definitely need a group to build strategy around education. You all need to be educated and primarily in intersectional labor organizing, decolonial theory, anti-racism, non-violent communication, and personal and operational security. It needs to be the most important thing the chapter does, and it needs to be structured, planned, and strategic. It must adopt an ideological line, and anarchism isn't it. It can and should incorporate learning about anarchist tactics, because they are great tactics, but it cannot elevate the anti-statism and anti-structural aspects of anarchism.