"Where logic falls to the ground is, if she wants to reorder (she does), and she has all my contact info (she does), why (oh why!) is she waiting for ME to contact her to see if she wants to reorder?!?!?"

As part of the sale you made previously, she got it into her mind that you would take care of her.

"That TW, such a nice person he is, so helpful. I'm glad he's the one that I ordered from, I just know he'll be there in the future for me."

Given your personality, I'd have to wonder how she got that impression from you, but there it is. She figured you'd take care of her needs and call to check on her needs.

You inadvertently sold her on you. Figure out how you did that, and do it to someone else.