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You gotta shaft someone to max out the other bosses. Bad thing is they all have pretty crucial rewards. Cassandra gets you the guy who brings guns, Burke has the 'lose the cops' reward and car delivery, and Vito has the Mob Doc (more health, stamina).
OF them all Burke is the most disposable but his rewards just make stuff easier.
Unless you play all the way through the game, after you win then you can do additional unlimited side missions for each underboss (stealing week, stealing moonshine, or stealing stolen goods until they max out. I don't think you can do that until after you are done but I Honestly didn't try.
Its complete ♥♥♥♥♥♥♥♥ that the game dont explain that by itself. Beginner error of hangar 13...