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My guess is that it's asking whether something is good or not, similar to saying いいですか.

So my question is what form is this and what does it stem from?

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  • SE allowing identical usernames can sure be confusing at times. Anyway, questions about かしら have been asked several times before, and I recommend using the search function. See for example this: japanese.stackexchange.com/q/164/5176 – Will Mar 21 at 23:32
  • @Will Certainly is. For a second, I thought your comment was bot generated because it had found a duplicate question. Thanks for the link. – Will Mar 21 at 23:38
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As (the other) Will suggested in the comments, there are already several posts where you can learn more about the usage of かしら. As a short answer to your question:

Rather than いいですか, in most (if not all) situations it's better to think of it as a version of saying いいかも(しれない), e.g. after someone suggested something, it could be used as a response meaning like "a yeah, that might be good/work".

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