I think it is safe to assume - even with Harry eventually becoming head of the Auror Office and with his inheritance - that Ron, given that he co-runs an exceptionally successful business, ends up making more money than him.
So how much delight do you reckon he takes in insisting on paying the tab when they go out for drinks.
"You miss him!" Hermione said impatiently. "And I know he misses you —”
“Miss him?" said Harry. "I don’t miss him….”
But this was a downright lie. Harry liked Hermione very much, but she just wasn’t the same as Ron. There was much less laughter and a lot more hanging around in the library when Hermione was your best friend.
I like to think that this is when Ron decided not to ever worry about exams again.
Harry and Ron
After the statement by JKR yesterday, J-dawg text me a little scene that could have happened between Hermione and Ron. I changed it a little bit, but I scribbled it out this afternoon.
"Listen to me!" said Harry, almost angrily, because Ron and Hermione were both smirking now. "Just listen to me, all right? It sounds great when you say it like that, but all that stuff was luck — I didn’t know what I was doing half the time, I didn’t plan any of it, I just did whatever I could think of, and I nearly always had help —" Ron and Hermione were still smirking and Harry felt his temper rise; he wasn’t even sure why he was feeling so angry.
"Don’t sit there grinning like you know better than I do, I was there, wasn’t I?" he said heatedly. "I know what went on, all right? And I didn’t get through that because I was brilliant at Defense Against the Dark Arts, I got through it all because — because help came at the right moment or because I guessed right — but I just blundered through it all, I didn’t have a clue what I was doing — STOP LAUGHING!"
The bowl of murtlap essence fell to the floor and smashed. He had become aware that he was on his feet, though he couldn’t remember standing up. Ron and Hermione’s smiles had vanished.
Ron and Harry’s imaginary predictions for their Star charts in Divination which actually happen during their fourth year. - Harry Potter and the Goblet of Fire (Page 196)