In a way, it's almost easier for me (emotionally, I mean) to ship pairings where there's NO CHANCE it could happen, because if I ship something like NaruHina, where half of it ACTUALLY DOES want the other half in an obvious way, it can be sort of heart-breaking when it's denied to them.

Exactly. It's the hope that a pairing I like will get together being dashed that really kills me, and then while I understand the validation of having a pairing made canon, I have too many ships that I've loved until they took that step, and then I hated them.