1. Nobody including the flight crew knows where he jumped. 2. The plane crossed the Columbia upstream from where the money was found. Cooper got on the plane in Portland, and that is where he had to get back to. He certainly would not have wanted to jump out over the Washington forests 50 miles away from civilization, and then spend two or three days walking, just to get to a small town, where everybody would already be looking for him. He would have waited until he saw Portland and the River, then he would have jumped. Good plan? Probably not, since it looks like he drown, and his body and most of the money ended up on the bottom of the Columbia, except for a few packets of money that got loose and floated to the Tena Bar.
They know when the aft door opened, 8:00 pm, and then the plane shifted, which they interpreted is when he jumped at 8:13. That is how they got the search area. If he had jumped later then he would have perhaps landed in the Columbia. The money falling upstream in the Columbia would mean it fell closer to Portland. So either some money was caught somehow, or he jumped with it much later. I do agree, most likely he died.