Rulings

Raid abilities care only that you attacked with a creature. It doesn't matter how many creatures you attacked with or which player, planeswalker, or battle those creatures attacked.
Raid abilities evaluate the entire turn to see if you attacked with a creature. That creature doesn't have to still be on the battlefield. Similarly, the player, planeswalker, or battle it attacked doesn't have to still be in the game or on the battlefield.
Count the number of attacking creatures when the last ability resolves, including Wingmate Roc itself if it's still on the battlefield, to determine how much life you gain.