You may consider renting a car at PDX and driving to Ashland. You will already have clocked lots of time in an airplane.
Here is one of the entrances.. Even if you don't "need chains" ...
Crater Lake will likely be snowbound. This winter is looking to be colder than usual according to reports I have read.
You might try contacting Menucha, a retreat in the beautiful Columbia River Gorge (in Corbett overlooking the river)
I have no idea the ...
Embassy Suites is my go to.
Marchesi Vineyards in the Gorge have Italian style wines. I love it there. Owned by a first generation Italian, he knows wines.
I was told by taxi drivers that they must pay airport fees to access airport pickups. Perhaps Lyft won't pay the fees?
It depends on your skill level in driving. I have friends who do it yearly and have not had a problem except delay once in a while closed roads.
But yeah, You...