Maybe it's just me, but I actually thought that Tony's recording should've contained less talk about his feelings and regrets, not more. After all, he made that video as his final act as director of SHIELD. The point was not to apologize to his friends or talk about how sorry he was or fixing his personal relationships -- the point was to determine how to deal with Osborne. That's why Tony spent so much time talking about everything he's done to incapacitate HAMMER, and about how Osborne would act in the future. I think as far Tony's concerned, whether or not to reboot him should be a tactical decision, not a personal one, so when he said "can you forgive me?" what he was really asking is "will you be able to work with me if you bring me back, or are we all going to end up at each other's throats again while Norman runs around unchecked?"

I do think Tony needs to do a lot of fence-mending with the other superheroes, especially Thor, but that's something he needs to do in person after he comes back, not via recording.