I chatted with Dean for a while in the Silverton Library, when he was just beginning his CT trip, and I was nearly finished mine. We were both in town for resupply.
I enjoyed reading his blog, but I definitely felt differently about the “experience”. Despite a heavier pack, greater daily mileage, and being solo for the first half, I didn’t feel as challenged by it as he seemed to feel, even though I didn’t train much for it beforehand. Everyone is different — so don’t let his account discourage you if you want to do the CT — you may find it a lot easier than he did. For me, the biggest challenges were my boredom with the “green tunnel” areas in the first half (I need views to stay motivated, I’ve learned), and the mosquitoes/flies (which were mostly gone by the time he was on the trail).