So I had a great time scouting trails. Only vehicle problem was my door which kept unlatching on me. Need to adjust that before I fall out on a trail somewhere.
Beautiful weather and gorgeous scenery.
I have a couple of suggestions for the first leg of your trip:
Firstly, bring spare air filters.
Very, very dusty. How many vehicles are coming?
We drove for a day and a half (with various stops for photos and trail-finding) and made it from Hoodoo to Century Drive just west of Bend. Now that I've done it once, I'll be able to get you through this section quite a bit quicker.
I would also suggest starting at Mackenzie Hwy west of Sisters rather than go all the way to Hoodoo which is a popular OHV area and the dust is made worse by the recreational traffic. The roads from Hoodoo are wide and not challenging and (in my opinion) are only really worth doing when there's standing water to make it less dusty and more interesting. You do get good views of Mt Washington, but there are more majestic mountains further south.
Just my 2 cents and I have about another 5 cents worth. PM me.
Rohan.