Here are the Robbie ideas I had! You can always change them too.
1. Maybe Robbie lost his home to the explosion or whatever large harming thing caused by the transcendence happened, and he and his family don’t have enough money to get it rebuilt. Robbie becomes a VERY depressed street performer. Maybe basing his songs on his dispair and loss.
2. Robbie gets so desperate for a home or money or just plain help that he summons Alcor. Then blames it all on Alcor now that he knows he was in the center of it all. Hates him even more when he knows that it’s dipper. Dipstick has a dilemma on whether to help him or not.
3. If dipstick offers his help, Robbie might refuse anyway due to trust issues until his situation gets worse (maybe street gang ruining his instrument that he has to make money off of?), and makes the decision last second. He doesn’t recieve much, but it is at least a home and something to live off of.
4.Maybe Robbie and dippy start to get along better… notice each other’s strength instead of each other’s flaws, and understand each other better. It wouldn’t be for a long time though.
More may be coming!