Look, our failed attempt at the Cumberland Passage Permanent (CPP) was wet and cold and stupid. Like seriously it was exceptionally stupid. And that, really, could be that. Like period, end of story. The thing is, some of what happened to us was not actually our fault. Some of it was patently our fault. And some of it was 'Other,' as in somewhere between our fault and not our fault. And some of it was straight-up beyond fault of any kind, like what's beyond an act of God?, whatever it is, it was that: e.g. the night before our start, our gracious crew-of-ten-hosting host in Pittsburgh poisoned all of us with a semi-mandatory Last Supper of violent diarrhea-inducing Vegan Stew. I mean, not in our wildest dreams did we see that coming and I live in the Alberta Arts District in Portland, Oregon.
What I'm trying to say is this: do it (see Beta below), just don't do it like us.
Before we get specific, we all know who the elephant in the room (EitR) is, the elephant is Sandy, the deadliest and most destructive hurricane of the 2012 Atlantic hurricane season, the one that dropped 1-3 feet of snow in the Appalachian Mountains, the one they called a Nor’eastercane and Frankenstorm. That said, Category 3 Hurricane or no Category 3 Hurricane, it’s stupid to plan a bicycle ride from Pennsylvania to Maryland over the Eastern Continental Divide in October. I mean, that’s just a fact. For one thing you don't have to be Mr. Bob Almanac to know the Alleghenies have been getting dark & cold every October since roughly 480 million years ago. There are some other things too, but who cares when the first thing is that it’s guaranteed to be dark & cold?
Also, and this is not that big of a deal but it’s relevant I think. Riding close to 350 miles even in the best of conditions takes a really long time. At least I think so. I don’t actually know because I’ve never done it. Listen, coordinating these things sucks but you do some math and you make some informed estimates based on experience and anecdotal evidence, and you give yourself a window; in this case to make our exit flights we needed to be in DC T-plus 51 hours from our  3:00 AM start, which in August in a dry, temperature-controlled environment, when and where the plan was made, seemed reasonable. It wasn’t.
Side Note: We planned the ride for Halloween night. Which, based on what we know about Witches, Tricks and Treats, Hessians, Hunting Season, the Occult and SRAP (Satanic Ritual Abuse in Pennsylvania) was at the very least an auspicious or inauspicious (whichever one is the bad one, I forget) twenty-four hour period during which to travel through sparsely populated Appalachian woods not that far from where Blair Witch Project was filmed. So yeah, factor or not, that one was definitely on us.