"It is peculiar, because a plain reading would indicate that perhaps the Court is implying that people who are affiliated with state-regulated militias might not have individual rights under the Second Amendment."
Possibly, but if the SC wanted to imply that, why not just limit the question to:
“Whether the following provisions — D.C. Code secs. 7-2502.02(a)(4), 22-4504(a), and 7-2507.02 — violate the Second Amendment?"
Why do they include the positive assertion "Second Amendment rights of individuals" if there is ANY question in their mind that the Second Amendment does or does not apply to individuals? If individuals do NOT have those rights, then why assert it as fact? In other words, the way the question is phrased does not allow the SC much latitude or wiggle room to rule otherwise. By limiting the question, in the manner above, they would have squelched all speculation of their intent and afforded themselves a wide range of possible rulings without tipping their hand.
OTOH, perhaps they just wanted to stir up a hornet's nest in an election season so they could sit back and enjoy the fireworks, LOL.
You have made very good and thoughtful observations; thank you.