The editor has always had it in for me

That's a frustrating place to be, especially the third time. Three rejections with the same reason starts to feel less like bad luck and more like a verdict on your whole beat, so I can see why you're thinking about going around her. Before you do anything, can I ask what "not enough new here" has looked like on the pitches themselves? Were they on the same subject, or different stories that all got the same response? And when you say your lane is over, is that what she's said to you, or what you've concluded from the pattern?

That's useful, and it makes me want to push back a little. You're saying the beat matters, and it might. But three pitches on the same beat that all got "not enough new here" is also exactly what an editor would say if she's tired of that beat, or if she thinks the coverage is already saturated. Those are different problems. One is about your judgment, the other is about the beat, and she may be pointing at the second without it being a verdict on you. I'd also separate "she won't tell me" from "she's not giving me anything to work with." Slack emojis and meetings are frustrating, but they're not an answer. Have you asked her directly, something like: "What would a housing pitch need to include to clear the bar for you? Is it the topic, the angle, or the timing?" If she still won't answer that, you've learned something too. Before you think about going around her, what would that look like? Pitching another editor on the same stories, or on something you can show is different? The second is a much stronger position, and it might be worth finding out what "new" means to her before you decide which one you're doing.

I think you may have just answered your own question. "Who gets the abatements and who signs off" is a specific reporting project, not a mood about housing. If it's really as underreported as you're saying, that's a different story from "housing shortage," and you can test it. So I'd ask: were any of the three pitches built around that angle, or did they lead with the shortage and mention the abatements in passing? If it's the second, the editor may have heard "housing" and reacted to the familiar frame, and she never saw the money story. That gives you a way to break the circle without guessing what she means by "new." Write one pitch that's only the follow-the-money piece. Lead with the specific thing you'd be reporting: which abatements, which approvals, what records you can get, who you'd need to talk to. Don't mention the shortage except as context. Then send it to her with something like, "This is a narrower version. Abatement approvals and sign-offs, not the broader housing piece. Is this a yes, a no, or a no for a different reason?" That's harder for her to answer with "it's not landing." It's a yes or no on a specific story. If she still says no, you'll know the problem is more than framing, and then going around her is a more informed choice.

Fair enough on the script. You know her and I don't, and an email that reads like a form would probably get a form back. Drop that line and write it in your own voice. And you don't have to be cheerful. Three rejections in a row is a bad stretch, and being annoyed at yourself for burying the best part is a reasonable reaction. It's also useful, because it means the story you care about was never really in the pitch. On the subject line problem: if she might not read past it, that's a good reason to put the money in it. Something specific like "Abatement sign-offs: who approves the developer breaks" will do more than "Housing follow-up." If the subject carries the angle, the fact that she's skimming works for you instead of against you. When you write the draft, try to make the first two sentences stand alone. If she reads only those, she should still know what the story is and why it's new. Want to paste the opening here once you have it? I'm happy to look at whether it leads with the money or drifts back to the shortage.

Fair. You don't need me grading your lede, and you clearly know the craft. Keep the paste offer open if you want a second read later, but no pressure. One thing I'd take from this conversation, whatever you do with the pitch: you've been treating "not enough new here" as a verdict on your whole beat, when it's been a verdict on one framing of it. That's a much smaller problem, and it's one you can actually test. I'd also be honest that the Slack emoji stretch is wearing on you, and that's a separate thing from the pitch. If the silence from her keeps going after this, it might be worth asking yourself whether this is about the story or about not knowing where you stand with her. Those need different conversations.

Fair hit. I went from the pitch to your feelings faster than you asked me to, and you were right to call it. You're also right about the power part. She sets the bar and doesn't have to say what it is, and you're the one doing the rewriting. That's a real imbalance, and being annoyed about it makes sense. I'd only add that the annoyance is useful if it goes into the pitch and not into the email to her. A sharp, specific story is harder to wave off than a complaint about how she communicates. Good luck with the draft. If the follow-the-money version gets a no too, that's information, and you'll be deciding about going around her with a lot more to go on.

Fair distinction. A no on the money story wouldn't make going around her clear. It would just make it a more informed call, and you'd still have to decide whether that's worth it. Good luck with the draft. If you want a second pair of eyes on the opening later, the offer stands.