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Steve Rogers hasn't really had a particularly easy life. He's struggled along, he's proud of himself, he's self-sufficient and capable and he works damn hard. He has friends and a purpose and he's only a few semesters from graduating college. He's managed, but his life has been far from easy.
That's mostly because of a slight filing error.
The last thing that Steve needed was someone to watch over him. The only thing that his Guardian Angel needs is a second chance to make a first impression.