Marshall - Everyone has to deal with losing a parent. Yes it was painful. But it wasn't a pain that lasts forever.

Lily - She just liked being comfortable and cosy in her regular life that when a baby was brought into it, her comfy and cosy life went into disarray. It's also not a pain that's lasts long. One your baby grows up your gonna love it to death.

Barney - Growing up without a Father is a pain that's gonna stick with you forever. It's encased in your mind and has a direct effect on your personality too. It's a pain that lasts.

Robin - Not being able to bare children is a pain that's gonna stick with you till you die. Yes there are other ways, but knowing you can never go through a pregnancy is enough pain in its own right. It's a pain that lasts too.

Ted - Loneliness is something that's temporary, Once you meet one of your friends you are cheerful again. Loneliness is only painful when you're alone, so it's kinda irrelevant. But we gotta give it Ted. HE IS THE MOST EMOTIONALLY STABLE PERSON I'VE EVER SEEN, even though it's a drama series. He's got the mind to withstand it all, so I'd say that kinda emotional injuries can leave someone else scarred for life. That pain is also something that lasts.

So concluding my analysis, I'd say Barney is most hurt, then Robin and then Ted. Barney > Robin > Ted.