While I'm a proponent of them avoiding Helton's contract, I think the risk is minimal and they should extend him now. First of all, it's only a one year deal, and doing it now shuts the competition out. Second, I'm not that sure that Schilling is in deep regression. He's certainly not the power pitcher he was 5 years ago, but he's also changing his approach. Despite his weight, he works hard at his craft, and I don't have any doubts that he will be able to develop the feel and command for more pitches in his reportoire, like his new change up.
Plus, the guy put his career on the line and delivered the prize. I know, I know, they don't want to pay players for their past performance, but I don't think the risk of him tanking is all that great, and, sometimes, you need to make exceptions. If anyone is worthy of an exception, it's Curt.