In my opinion, judging by the political landscape of New Vegas, I suspect Benny and the Chairmen's first goal would be getting out from under Mr. House. Benny also was obviously a big advocate of a "Free Vegas." Quests would likely involve forming/co-opting caravans for import/export, perhaps shoring up problems from Benny's past (maybe some old enemies are looking for him from his tribal days?) Cleaning up some of the suburbs of New Vegas, since assuming Benny is somewhat of a throw-back to the Vegas mobsters of the 50s, he wouldn't like the filthy culture springing up right outside the gates of the North Strip. Specifically, I believe Benny would likely try to expand his influence. Not to shut-down the other casino's as that would be counter-productive to the Vegas image, but to kind of put the Chairmen in the position Mr. House held. Perhaps the quest would be to get the Lucky 38 back up and running? While this is out of the scope of the mod, if Benny were real, from a business development aspect his first priority would be getting some sort of relatively safe transportation system running between population centers. At very least schedule convoy's to bring business in from outside the Mojave.