To get back to the OP's original question, you might want to pick up a cap with LEDs built into the brim or a LED unit to attach to a cap you already own. I've not tried either of the products to which I linked, but I think a light that is easy to keep at hand and doesn't require holding in hand would be best for getting rid of the dark while reholstering.
I carry a Glock 26 AIWB and when I reholster, I slide my weak hand in behind the holster, tilt it away from my body, and then insert the pistol. It's slow and I have to pay attention to where my feet are. I'm sure I'm not 100% compliant, but I can't think of a safer way to go about it. Also, I never, ever reholster while sitting.