Howdy, I helped develop the route with Donnie last year.
The route is rather easy to follow. Most intersections are marked. Wayfinding shouldn't be a problem, but I'm sure lose a few folks to the dingos anyway. There really isn't *that* much climbing. The section between Prineville and Shaniko has by far the most, and 2 of the big climbs in there are paved and decent grades. I rode the whole thing with an 8sp Alfine and walked on one short section.
Sag support: VeloDirt isn't providing any. But Amtrak provides a sweet train ride between Portland and Klamath Falls. And Portland Sag Wagon is offering some shuttle services during the ride:
http://www.portlandsagwagon.com/Site/Blog/Entries/2014/3/1_Oregon_Outback.htmlMake both those reservations ASAP, and remind Amtrak that you are one of a couple hundred people that will need to ship a bike that day.
Also, highly recommended is Cowboy Dinner Tree. Which requires reservations as well. I'm not saying it's impossible to do the Oregon Outback without a 30oz steak in your belly, just that it will be much, much harder.