Well, they don't call it Tombstone Pass for no reason.
It is doable but rather steep and windy. Road condition could be better. A lot will depend on your driving comfort.
IMO you would be better off to take OR 22 to I-5 then south to 34/20. Or 126 then I-105 to I-5. Both nice drives except for the freeway. Bad part is both of these routes were burned badly last year so you'll see lots of black and minor delays.
DO NOT take 242 out of Sisters. Open summer only. Narrow lanes, rough, and low branches. While you are under the length I wouldn't do it. If you do have a toad send a night in Sisters or Bend and day trip it. There is an observatory at the top short walk to top and well worth it.
https://www.fs.usda.gov/recarea/will...ea/?recid=4403 Great views if you hit a smoke free day. You can also make a loop back to Sisters.
EDIT: To clarify I am referring to Hy 20 west of the 126/22 split at the bottom of Santiam Pass.