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The T-shirt cannon from Robot Chicken was pretty funny, but I don't think Boba should have it. Doesn't really go with his character, you know?
As for Calvin/Fumbles, he'll do just fine in Remnant. I bet he could even kill Hazel if he was well hidden and was the first to go down. As long as he keeps his ego in check and doesn't 'fumble', he would do good.
I would have to say Fives. Sure Jesse was reprogrammed and killed after everything, but Fives was the only one who knew what was going on. But the worst part was that nobody believed him. Even Rex wasn't exactly sure what was going on until it was too late. Fives stood alone and he didn't win.
As for Pyrrha, that's a good question. I think if she fought against him, her Semblance would help her win easily. His actions of killing people would be questionable, but I think she would open up to him one she learned that he was looking after Grogu. As for Ironwood, I'm not sure what she would do. Everyone else didn't seem to think he was so trustworthy at the time, but she might realize what those consequences were. But given how far Ironwood went into the deep end, she would definitely side with RWBY.