These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Darry could count as something of a Jerkass Woobie, since although Ponyboy is pretty well convinced his brother doesn't care about him, and he can be pretty cold and harsh at times, he's still trying quite hard to keep his family together and gave up a lot so that they'd get to stay together. Despite the way he acts sometimes, it's hard not to feel sorry for a twentysomething guy who's lost his parents and suddenly has to head his family.
It's also important to remember Darry was college bound before his parents died. While he couldn't fully afford it, he was smart (and poor) enough to get scholarships. Instead, he didn't go to college and is struggling to keep his brothers from being trapped like he is.