Every time I go through this, the Lord is faithful to show me that I am His, that I am serving His purpose and that He loves me.
I think it's important to keep asking these questions, even though I battle feeling like I should know the answers after all this time. But, I think the Lord wants me/us to ask Him often. He wants to show us that he cares deeply about us specifically and especially.
I don't have much to add beyond this thought. I felt like it was worth sharing. The end.