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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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".