I'm probably going to get shit for this here, but you have to meet people where they are. If elections are where they are, that's where you have to go. The best way to get people to work with you will always be working with them first. That's going to involve doing shit that you don't want to do. In the same way that a good teacher in school is in a two-way relationship with students, effective organizers don't organize at people, but build meaningful and mutual relationships with them. People will open up to you when they feel you're open to them.
So my advice is to join the DSA work, do their elections, but take it upon yourself to keep up the organizational momentum once the election is over and work on something else. Yes, you're going to have to canvas for some shitty democrat, but, if you knock enough doors, you'll really learn the situation on the ground where you live, and you can roll that over, hopefully with a few friends. If your personal philosophy doesn't let you compromise enough to go that route, so be it, but that's what I'd do.
I just want to emphasize that to set up a truly independent and unpaywalled piece of media, you probably need to abandon hope of it being even a viable side hustle. Quasi-independent media on, say, YouTube or Substack can make some money, but you're then stuck on those corporate platforms. If you want to do your own website or podcast or whatever, that's more independent, but you're still dependent on Google if you run ads, or on Patreon if you do that sort of thing. The lesson of Twitter should make pretty clear the danger inherent to that ecosystem. Even podcasts that seem independent can easily get into huge trouble if, say, Musk were to buy Patreon or iHeart.
I've been writing on my website for over two years now. My goal has always been to be completely independent of these kinds of platforms for the long term, no matter what, and the site's popularity has frankly exceeded my wildest dreams. For example, I'm the #1 google result for "anticapitalist tech:"
But I make no money. If I wanted this to be anything but a hobby, I'd have to sacrifice something that I think makes it valuable: I'd have to paywall something, or run ads, or have a paid discord server, or restrict the RSS feed. As things stand now, I don't know my exact conversion rate because I don't do any analytics and delete all web logs after a week, but I did keep the web logs from the most recent time that I went viral (top of hackernews and several big subreddits). I made something like 100 USD in tips, even though the web logs have millions of unique IPs. That's a conversion rate of something like 0.00002 USD per unique visitor.
Honestly, if I got paid even $15/hr, I would probably switch to doing it at least as a part time job, because I love it. Compare that to the right wing ecosystem, where there's fracking money and Thiel money just sloshing around, and it's very very obvious why Democrats are fucked, much less an actual, meaningful left. Even Thiel himself was a right wing weirdo before he was a tech investor, and a right wing think tank funded his anti-DEI book. He then went on to fund Vance. It's really hard to fight that propaganda machine part time.