Warmaster Horus
Explorer
PHB, Pg. 177, Left Column under Hiding states:
"In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen."
PHB, Pg. 182, Right Column states:
"When travelling at a slow pace, the characters can move stealthily. As long as they're not in the open, they can try to surprise or sneak by other creatures they encounter."
So the player's basically says... ask your DM.
Obviously it should be considered that you are not approaching. You're just popping out to shoot. But you ARE popping out. In the open. Against an enemy that knows you were just there a second ago.Personally, I'd absolutely say you could get sneak attack damage, and get the re-hide. That's fairly cut-and-dry. The question is if you get advantage when you pop out again.
I'd personally say the enemy gets a perception check when you pop out, depending on the lighting, the amount of distractions, and if you've already peppered the same guy with one or more similar attacks from the exact same position. If there's really no reason for him to NOT be able to see you, then he sees you. And you don't get advantage. Simple as that.
Something to keep in mind about Hide this edition guys. It's not invisibility. Read pages 177 and 182 very carefully. There has to be environmental conditions that allow you to be hidden in order to become hidden and stay hidden.
And when he does pop out, as long as it's not in the clear, but from cover, it's his stealth check vs his opponent's perception. Hiding != Invisibility, it equals his skill against another's.