Besides the fact that they (Hashirama and Madara) never held hands, the reason why Obito was so horribly redeemed is because his younger self "resembled" Naruto in so many ways and Kishi wants us to continuously sympathize with Naruto and his determined innocence while showing us that sometimes people can lose their way but the ever unfailing Naruto can set them right again. If you can recall the exact same circumstances set up the same weak attempt of redemption for Nagato because he too was very much like Naruto in the past. Although Nagato was never forgiven Kishi did try to build up sympathy for his character by having him laughably revive everyone he just killed in the village because of a book title.
Obitio (who was very much like Naruto) sacrificed his life to help Team 7 defeat Kaguya.
Nagato (who was very much like Naruto) revived everyone he killed with the exception of Jiraiya.
Itachi (who is now being shown compared to Naruto) supposedly prevented a war between the clans by massacring people.Madara did nothing to be redeemed and that's why he and pre-timeskip Orochimaru are some of the best villains in the series because they're just…bad.
Yet why give him the "pleasant passing happy ending?" A guy that caused so much crap and you have him pass away with his lover. Yeah, if that's not Kishi attempt at saying "hay, he's totally NOT THAT BAD. In fact, I dare say he's a decent guy. Redeemed in all your eyes right?" Same goes for Orochimaru "He's not that bad. In fact, he's kinda like your neighborhood goofy pedo uncle. Look how funny he is. Har har har!" Not sure if he gave Orochimaru a redemption moment, but Kishi sure did try to put him in a "not so bad" guy category like what he forcibly did with Madara.
One often thinks turning bad guys into good ones is an easy thing to do but…no, it's not. It requires a fair of development (instead of "HAY, he's just like Naruto guys. Can you see it? Yup? Okay, I don't need to go any further than that"), some shades of gray, and some tricky narrative maneuvering. Nagato was fairly stupid, Itachi was retconned terribly into being a "good guy", and Obito is simply the worst based on the fact that he was redeemed completely (to the point that he was put into that "cool guys" panel while Iruka was insultingly shoved off). I'm just baffled by the fact that Kishi doesn't grasp the idea that doing "one final good deed" doesn't automatically redeem someone with a history of causing misery to the extent that Obito did. That only puts them in a "dark-ish gray zone" rather than "good guy" zone. It would be like Hitler running into a burning building to save a puppy only to die of third degree burns in the hospital. He's a good guy right? Yup, completely absolves every crap he has done before hand.