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The comics make it clear that John was aware of the danger to Sam by that point, but I don't count them as canon.
I think Dean at 14 would be far more willing to embrace how much it hurt him to have Sam leave, especially since Sam would have been an even more stable figure in his life than John had been. Sam leaving a 14 year old Dean wouldn't have the same emotional impact of Sam leaving Dean at 22 and on top of that, since John wouldn't stop hunting, it would mean that Dean would be left by himself for days or weeks while John was away. In canon, Sam and Dean had each other at least. So yeah, definitely think Dean would resent Sam a lot more for leaving. I don't think he'd actually hate him, but he might tell himself that it was hate. And I doubt John praising Sam to strangers on the hunt would help much at all.
As for John raising Dean, hm... Dean would be 14 at that point, after all. Maybe John would have left him more often with Jim or Bobby? Or maybe it would make Dean drop out of high school even earlier so that he can just stay with John all the time. He might be a much better hunter as a result, because he would have been hunting full time from age 16 or so whereas in canon, Dean had to stay behind with Sam most of the time.
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