Maybe Sam initiates something (research? general hunt efficiency?) on his own that particularly impresses John? Enough so that when he messes up somewhere else as he almost inevitably will (PT, weapons) it still carries through? Or John and Dean have to leave for a day or two (training? hunt? recon?) and Sam is left on his own with a set of very specific tasks and he manages to complete all of them either to John's satisfaction or close enough that John knows he was really trying?
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Maybe Sam initiates something (research? general hunt efficiency?) on his own that particularly impresses John? Enough so that when he messes up somewhere else as he almost inevitably will (PT, weapons) it still carries through? Or John and Dean have to leave for a day or two (training? hunt? recon?) and Sam is left on his own with a set of very specific tasks and he manages to complete all of them either to John's satisfaction or close enough that John knows he was really trying?