why is my gamepass handler not giving players the items?

The way your code is written, the first gamepass that the Player has purchased, in the order you have typed them, is the only one they get. elseif doesn't trigger if a previous if or elseif in the same 'tree' triggered:

pcall(function()
    game.Players.PlayerAdded:connect(function(player)
        if game.GamePassService:PlayerHasPass(player,574426548) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 10
                    char.Humanoid.Health = char.Humanoid.Health + 10
                    game.Lighting.WoodenSword:Clone().Parent=player.Backpack
                end
            end)
        end
if game.GamePassService:PlayerHasPass(player,574427239) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 25
                    char.Humanoid.Health = char.Humanoid.Health + 25
                    game.Lighting.SubspaceTripmine:Clone().Parent=player.Backpack
                end
            end)
        end
    if game.GamePassService:PlayerHasPass(player,574430612) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 50
                    char.Humanoid.Health = char.Humanoid.Health + 50
                    game.Lighting.EpicKatana:Clone().Parent=player.Backpack
                end
            end)
        end
    if game.GamePassService:PlayerHasPass(player,574437515) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 75
                    char.Humanoid.Health = char.Humanoid.Health + 75
                    game.Lighting.RayGunBio:Clone().Parent=player.Backpack
                end
            end)
        end
    if game.GamePassService:PlayerHasPass(player,574439700) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 100
                    char.Humanoid.Health = char.Humanoid.Health + 100
                    game.Lighting.Phoenix:Clone().Parent=player.Backpack
                end
            end)
    end       
    if game.GamePassService:PlayerHasPass(player,574441188) then
            player.CharacterAdded:connect(function(char)
                if char:WaitForChild("Humanoid") then
                    char.Humanoid.MaxHealth = char.Humanoid.MaxHealth + 200
                    char.Humanoid.Health = char.Humanoid.Health + 200
                    game.Lighting["Ro-Orb"]:Clone().Parent=player.Backpack
                    game.Lighting.Darkheart:Clone().Parent=player.Backpack
                end
            end)
        end
    end)
end)