Using RondePDX as a Training Ride

I am writing this in the room closest to the front door where I await UPS delivering my Atlantis from Rivendell Bicycle Works.  I leave for VA in mid June and I am contemplating attempting the RondePDX legendary route for training purposes.  While I know it seems silly, I do recall the mountains.  It seems silly as I am no longer starting in OR and won’t see the first set of hills now until day 5 when I cross the Blue Ridge Mountains.

And I still wonder if this applies That wound will never fully heal. He will carry it the rest of his life.