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For Jacket specifically, I think he fits the universe reasonably well (considering the fact that he's canonically not the real Jacket and just a copycat, alongside the idea of the HM series being fictional in the Payday-verse -- see the arcade machine in Jacket's room -- and the fact that the Hotline Miami heist was canonically part of the plan to break Hoxton out, all things that integrate Payday!Jacket into the universe more than most heisters), he was one of the most beloved crossover characters in PD2, and unlike, say, Scarface, his rights should be reasonably affordable to keep around long-term so he's probably fairly safe as far as crossovers go.
There's a couple of question marks, though:
- Overbreeze and Dennaton were friendly in 2015; is that still the case over 8 years later?
- Is Hotline Miami being "finished" with no new games on the horizon an issue? (Jacket was added as part of HM2's release)
- Is Dennaton even interested anymore? (They've clearly moved on from the HM franchise)