[djshawk]

It looks to me like you are going to get more value from CO than the reg so I would bet less to intice him along. If he's got a small pair it's going to be way easier for him to call 2 smaller bets than a shove.

If you bet 50 you're giving them at most 3-1 implied odds which isn't enough to call with flush or straight. If you get a caller then the turn will give them 4-1 so still only breakeven to hit their flush and you made money on the flop call.

If you think shoving will be interpreted as weak and will get a call then fair enough but I don't think the reg will have a big enough hand to make a hero call here and the overbet will probably scare CO off.