I love the dynamic between these two where you can tell Howard loves Tony and Tony probably can tell but sometimes it's not enough.

I think that Howard shows his love in doing things and providing things, in a very traditional Alpha Male, Breadwinner fashion that would have been common in the era he grew up in (and even more important to him because he grew up with so little and can give Tony so much), but that Tony is too young to realize that, and needs to be told that he loves him and is proud of him and that he's doing all right. I kind of wonder if Howard had lived longer, until Tony was grown-up enough to understand him better, if they would have eventually worked things out. But I can also see Jarvis providing a little of that verbal praise with a quiet 'that was very well done, Master Tony' that makes Tony feel good about himself.

Thanks so much for reading and commenting!