I think that the unstated assumption here is that we don’t realize what people find difficult about using our tools because we don’t find it difficult, but I think it’s actually really hard to get the information we want here.
In some ways, people already involved in Python packaging are the perfect people to ask about it, because we’re the ones dealing with a diverse group of users, dealing with bug reports, etc. We also tend to do the most complicated things with packaging and know the right way to do things. Also, many of us were motivated to get involved in packaging to fix problems we had ourselves.
I am not saying we should ignore our users (quite the contrary), but I also think that we need to acknowledge that often if you ask beginners whether they like X or Y, they’re often making that choice without a deeper context, and in the end we would get a worse experience by taking them at their word. (I say this as someone who has made UX suggestions that were accepted in beta tests and come to regret them enough times to feel hesitant about it.)
I don’t think we should be polling people for preferences. I think if we can agree that the question of which way to specify dependencies comes down to (or would be significantly be informed by) a disputed factual question, we should come up with a strategy to determine the truth.
That said, I’m not convinced that our differences really come down to factual questions. People don’t usually complain or have problems with PEP 508 and they don’t really complain about
poetry's way to specify dependencies. That suggests to me that both are good enough and that people won’t be actively confused by using either one. Given that PEP 508 is already standardized, already in wide use, we cannot deprecate it in favor of a TOML-based system (which won’t work with all config systems) and people will need to learn it anyway makes me say that a tie should go to PEP 508. Maybe the result would be different if we were designing this from scratch in a vacuum, but I find it much more plausible that people will lament the proliferation of ways to declare dependencies than they will lament the fact that we’re using a compact DSL.