How do I handle HR compliance gray areas across many states?

You handle standard compliance well now, but the gray areas and the multi-state tangles still worry you. That worry is appropriate, not excessive. Clear rules are easy; the gray areas are hard precisely because there is no single right answer printed anywhere, and different states pulling in different directions multiplies the uncertainty. Feeling the weight of that means you understand the stakes. In the gray areas, the goal is not certainty, because certainty is not available. The goal is a sound, defensible judgment: you gathered the facts, you weighed the risks, you consulted where needed, and you chose the most reasonable path. That is what good compliance work actually looks like when the map runs out. And no one is expected to hold every state's rules in their head; knowing when to check and when to ask counsel is part of the skill. When a gray case lands, write down your reasoning and who you consulted before you decide. That record protects you and sharpens your thinking. You will not always be certain. You can always be careful and clear about why you chose as you did.