The money is waiting. I'm in the same boat JHO. You would think that in all my concert experience over the past years, this is nothing for me. I've never never never ever dropped $1,500 on two tickets.
It's a crowded boat, because I'm in it as well. Seeing just how much cheaper GA tickets are is making me consider if VIP is truly "worth it", but I figure I've done the GA experience many times before -- VIP will be a way to make the Bonnaroo experience fresh again, so why not go for it!?
There is a VIP entrance/exit between camp and What Stage. It's much easier to pass through than the GA gate (you'll see!). I've never had my pack searched although I know others have. Just be discreet and you'll be fine. If you try to walk in with a cooler, you'll probably be turned around! To get back to camp, the security guy will check your wristband which isn't a hassle either. I've seen some GA campers try to walk through but they are stopped. Makes me feel a little bit more secure. Less likely that a wook to lift your stuff