Oregon really messed up when they went with Oracle, and now we're going to be stuck with them forever. Oracle's a big company, but they're stuck in the past. And now, we're stuck there with them. We're going to be paying millions for the foreseeable future; the alternative is to dump CoverOregon completely and start over. Since our "leaders" have already dumped $100 million into a nonfunctional site, they can't really afford to start over. But they should. After all, wasting money has never been a problem for them, and there are never any repercussions.
As Wired points out, our "leaders" blew it by not actually defining the scope and requirements in the first place (they further mucked up by issuing change-orders). Change-orders are a bonanza for contractors working for government; a couple that I talked with a few years back confided that they'd convinced their boss to low-ball a bid for electrical work because the change-orders are what really brings in the cash.
But the state shouldn't have gone with an old-school company like Oracle in the first place; they're past their prime, and they don't use the tools that are now widely available to build scalable and functional websites. They should have asked how companies like Amazon are able to handle thousands of transactions per minute. Had they done so, they'd have realized that it's because they don't use Oracle.