Reverse order may ease day one.
Your first day will be quite exhausting following a 9 hour flight. I would think best case scenario you would not get to Bend until 8pm, a long day !! One way to go is to reverse the order of your trip and put less pressure on the start. Maybe head to Yachats on the coast and get an early night and then an early start to Crater Lake [6am] and finish in Bend and then drive to the Gorge and into Portland. It will still be tiring but at least you shouldn't be exhausted from day 1.
