"So I was rewatching supernatural for probably the millionth time. But I noticed that Benny, the vamp that rescued Dean from purgatory and saved Sam when doing the demon trials was also in season 2 episode 3. He's the bartender that gives Sam and Dean tips about the vamps. "

You are correct Ty Olsson plays the bartender in S2:Ep3-Bloodlust and is later casted as Benjamin "Benny" Lafitte.
In S2:Ep3-Bloodlust he is the Bartender "Eli" who is a member of Lenore's nest.
I am not sure if he is Benny going under an alias "Eli" like he goes under "Roy" in S8:Ep9-Citizen Fang where he works as a cook in the same resturant his Great-Granddaughter works.
So don't fret your eyes are not deceiving you!

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