Hmm, well Sonny would probably figure Dean out pretty fast and be shocked to find Sammy. They’d both work together to make sure Sam keeps out of trouble and out of the way of the other boys, and Sam would accompany Dean to school just like in BT.

Sonny’s farm in canon happens about a month after Sam’s curse hits, so at this point they’re actually discovering Oscar. Since there’s only one kid to support, money goes further and Dean didn’t have to steal bread for food.

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