Cheers for the insight Joe. Ok, Madras or Mitchell look like realistic and my highly-likely destinations. With sensible driving and an early-enough departure time out of Portland, it should be relatively easy (perhaps just as easy as catching a train..). Weather-permitting, I've no doubt the view towards Mount Jefferson mid-eclipse will be beyond words.
What I learned from Cairns 2012 - on the Esplanade with my extended family in tow for that early morning (after a night without sleep for me) - was that nearly everyone else "in the community" isn't remotely as excited to be heading outside for an eclipse, let alone bother to drive any distance. The roads around Cairns are limited, but I heard of no issues at all with regards to congestion or otherwise.
Nevertheless, I'll keep the option open of flying interstate should all of Oregon have a weather apocalypse at that time of the year next year.
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