There's enough hands that V3 can call (Axs, some Axo, 55) that the only question is how elastic is his calling. It is a late night game, so to me it is less about the cards and more about the player. The first question to ask is, "is he willing to buy more chips tonight?" If the answer is yes, a shove is the right solution. He'll reload. If the answer is no, then I'd look at whether he was ready to go home soon. If yes, bet big. He'll shove the next hand to finish the evening. If he isn't, then I'd go maybe $250. You need to make the bet such that he's got decent playing chips if he calls and losing. Otherwise, he'll nit up on you and fold to a big bet because he doesn't want to play short stacked.