Other commenters have added reasonable caveats for situations in which it’s okay for the conversation stack to grow tall, but I’ll add a buttress to your main point: when debating something important outside of rationalist circles, the stack size should be limited to 1, with 2 being a privilege. Only debate one point at a time, and choose the point that’s easiest to verify or falsify.
On YouTube, Reddit, Substack, and face-to-face, I’ve found that debating multiple points before the first point has been resolved usually results in continuously-shifting goalposts, or the interlocutor ignoring whatever I’ve said about one point to focus exclusively on the point where my response seems weakest.
I’ll emphasize that I consider this to be especially important when debating non-rationalists, because their pride encourages them to change subjects to show that they’re right about “the thing that actually matters”, and because the soldier mindset discourages them from acknowledging your strongest points.
This standard might sound harsh, and it does kill some conversations quickly, but I think that’s preferable to writing a comprehensive reply that accounts for all of their explicit and implicit claims, only for none of them to be acknowledged. In both cases, nobody is convinced of anything—but in the first case, at least I didn’t waste an hour or more.
When debating with rationalists, I’m much more lenient about discussing two or three points concurrently, because I trust that 1) they’ll give credit where it’s due, and 2) even if they appear to have changed the subject, they’re investigating a crux, and they plan to backtrack to the original point before long.
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