I wouldn't mind him leaving Emerica; it's his choice. I feel like they've exhausted all creative possibilities with him now at this point. They've given him every shoe he's ever wanted, he's came through with amazing video parts, clothing opportunities -- it's good mileage & possibly one of the most complete runs a skateboarder has had with any company in history. There's nothing really more for him to do for emerica.
The only disadvantage for him leaving is that he'll lose ties to emerica as a life long brand ambassador, whereas another company like Adidas, might dump him down the road.
I'd be interested to see what kind of direction Emerica goes in without their all-time great "brand leader", in Reynolds.