I think the main thing will be Duke and Steve as roommates which could either go really well or really Steve's got a headache. Duke has criminal tendencies of the smuggling variety from time to time but I'm not sure how much that'll come into play here. Either way, he's more of a 'has ..mostly good intentions but does things my way and not always in line with the law.' I've seen H50 through the first few seasons, so I at least have an idea of Steve but his later stuff I'm clueless about haha.
And then I've got Bucky who will know his most favoritest, chatty webslinging spider. Karen is from the MCU world, and being in NYC she probably has heard of Spider-man, but she won't know anything about Peter.
I don't know your other two, but mine are open for anything.