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I have a set of features that I want to develop into a site (or multiple sites), and I want to know how well Drupal fits.

  1. Would asking a question about that be on topic, if I provide details? (I suspect not - the FAQ has "Building a site from scratch" as being off topic, though I could interpret that in more than one way)
  2. If 1. is not on topic, would it be on topic to ask "Where I can get help with determining whether Drupal has a good fit with my requirements?"
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If you make the question very specific, then it is acceptable. The FAQ is referring to those questions where the OP asks a question about a generic feature.
I think that a question where the OP already created a Drupal test site, looked for the modules that would suit for the specific purpose the OP has in mind, and tried some modules already, is more acceptable. "Show your research" is a valid motto in all the Stack Exchange sites. That is different from questions such as the following (hypothetical) question:

I have heard Drupal is used from the USA government for one of their sites, but I have never tried installing it. Could I use it to make a site where I sell pictures?

Questions about resources, to which I include a question like "Where I can get help with determining whether Drupal has a good fit with my requirements?" are normally saw as not constructive, on Stack Exchange sites.

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