There's a bit of him that's relieved, and a bit of him that's upset when the Sorting Hat cries, "GRYFFINDOR!" because it's the House he'd hoped for, but it proves that he really isn't different from the rest of his family. He's so ordinary, so unspectacular that he can't even stray from the Gryffindor tradition. How pathetic.
But just because he isn't as special as the others doesn't mean he can't be that heroic Gryffindor the Hat says he is. And just because he's not clever or good at Quidditch or special at all doesn't mean he can't be courageous.
AN: I'm going to have a group of people angry with me either way, so I might as well have the group be rightfully angry with me. Allow me to state that I don't hate Ron. The reason it's repeatedly stating that he is so very plain is that it's from Ron's perspective. He's very insecure, I think, and I wanted to show that it my writing, you know? Hopefully I succeeded in that...