OP's choice.
Some think taking Hy 22, Santiam, around Big Cliff is worse thing ever. Some scream taking US 20 over Tombstone is worst thing ever. Others scream that Hy 58 over the Willamette too steep. I have done the exact route I discussed more times I can count.
The OP mentioned a stop near Bend even though he was just looking for a place to park. My guess is that the distance is all he wants to travel for a day. Going Hy 126 meets his needs, though it is a little longer and is a easy drive.
If I were to use the Newport-Bend route with Bend being the destination I would do 20 to 34 and rejoin 20 at Lebanon. Yeah the road over the hill is a little rough and windy but so what. But I wouldn't send someone over it that I don't know their driving ability.
Now if I was using the final destination of Crater Lake like the OP said, I would fell him to follow 99 to Hy 569/ Pape Bypass or whatever it was renamed to and take it to I-5 south to Hy 58 and continue on south on US 97.
If the OP is reading this there is also a casino and truck stop near Chiloquin. Fuel prices are good and I know you can overnight there. Not sure if they allow multiple nights.
Ed_Gee wrote:
Why in the world would someone steer the poor guy to the second largest city area in Oregon?! I recommend taking donn0128’s suggestion.