It says here that they went to that school in 1997, so Dean would have been 18 in that ep, and Sam 14. Dean said he dropped out of school/got his GED, so I'm guessing that not long after that, he dropped out and John gave him the car so he could leave Dean with Sam (and transportation) while Sam was in school, and still go off on his own hunts.
And according to THIS, not long after, Dean went to Cicero and met Lisa (the ep was 2007, so that would have put meeting Lisa 'over eight years ago' in 1999 or 1998). And we all know that Dean was driving on his own, 'five states in five days' while Sam and Dad were in...Florida? I think? Can't remember. Anyway. :)
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And according to THIS, not long after, Dean went to Cicero and met Lisa (the ep was 2007, so that would have put meeting Lisa 'over eight years ago' in 1999 or 1998). And we all know that Dean was driving on his own, 'five states in five days' while Sam and Dad were in...Florida? I think? Can't remember. Anyway. :)