I went back to the beginning (2011, apparently) for this. I'd been lurking a bit prior, watching the show as a 'regular' viewer, and I was just smitten, even w/o an exposure to fandom. The first fanart I posted here on LJ was for my best girl, monicawoe and her series "Theosis". Monica was really my gateway drug into SPN fandom and I never looked back!
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And my first fanfic: Kiss With a Fist is Better Than None. It's a bit dark *cough* and conspicuously artsy, but it had a few clever bits too, maybe? I sometimes debate going back and revising these older pieces but then I think "Nah." These are little time capsules of where we were back then, and how far we've come. If we go back and mess with them, it erases that history, that information. I'm not a particular sentimental person, but I think I like looking back at these things, such as they are, with a sort of wistful fondness. They're by no means great, but they have great spots. And that's enough for me. :)
How do you all feel about your older pieces? Do you want to rework them? Or do you feel like they are what they are?