I scouted some of that route, including Windigo Pass, in 2010 and led a trip 
there for Adventure Cycling in 2011.  Based on my knowledge I concur with 
avoiding Windigo.  It is not maintained and is best done with fat tires.  What 
many people take for sand is actually pumice dirt that will stick to 
everything.  There is not much scenery there and you don't save that many miles.

If you don't have reservations at Crater Lake Lodge you are probably SOL for 
this summer.  Especially if you are not going fully self contained it is 
essential to call ahead and confirm availability of water, food, stores.  Most 
of the services are provided by mom and pop stores that come and go.

Personally I would not stay in Bend but would do Sisters instead.  It's a small 
town with all the services you need, and is fun to walk around.

It's great country and you will have a fabulous trip!

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