TeaChat

Help a youngster out, I've drank oolong older than I am.

How does oolong's aging affect quality? If I found, say, a 2008 Dong Ding, would that taste better than a 2011 Dong Ding? Assuming the crop is the same.

"Better" not might be the best word. Different.
It all depends on the tea and how it was stored. It depends on your taste.
Many people like a little bit of age on high roasted tea to tame any smoky flavor. But some don't.
Some much older oolongs take on a medicinal flavor. Some people like this, some don't.
Some people will say that greener oolongs should not be aged. Some people will disagree.
Try to taste as many as you can and decide for yourself. Have fun.
Also, use the search bar up there. There are a few threads here on the subject.

I totally agree with everything Mike B just said. The key is finding what you like.

In general, the strong aroma of many oolongs will begin to dissipate with age. Since I love the scent of fresh oolong, I generally find that oolongs over a few years old aren't as satisfying to me. So I tend to drink greener oolongs soon after harvest and darker ones 6-18 months later. But that's just me. Many folks will say that any loss in aroma in an older oolong is compensated by additional complexity in mouth-feel, etc. I'm drinking a batch of 2007 Thief Poop right now, and it's very good.

Really old oolongs, say 1970s and before, often have a strong taste and smell of camphor. To me, this is interesting to try at least once, but I wouldn't choose to drink it more than rarely.

Good luck exploring!