The weather in the Daks and central NY has been MUCH better than normal for hiking. Temps and wind have been particularly forgiving for this time of year. Given the weather, he needed to be putting down 40+ mpd on the road to Pixley Falls, because he isn't going to make 34 mpd on snowshoes in the hills of western NY. He's developed acute tendinitis in either one or both Achilles tendons. That is most likely due to a lack of pre-hike training / conditioning. And that's going to be a difficult if not impossible injury to walk off now. A few days rest probably won't be enough, and the problem will likely reappear once he starts putting strain on the tendon(s) again.
As others also note, he's pretty arrogant about his ability to pull this off given that he obviously has no actual LD hiking experience. Kind of like somebody who has jogged a couple of times around the block in their neighborhood saying they're going to win the NY marathon this year.
This "trek" seems to be all about fancy websites, promotion, donations, and talk, with no more actual hiking than, as AS noted, an AT trail newbie would do. That, more than anything else, is why he's getting ripped by a lot of people, including me (I confess), at WB. It would be nice to see people display a bit of humility rather than being unabashed braggarts. People who go public with grandiose dreams should have the ability to deliver, or at minimum have the ability to POSSIBLY deliver, even though such an attempt would have the odds against it for the very best in the world. Sam doesn't have the ability. And yes, he is paying the price for his arrogance and total disregard for humility regarding his ability. The "naysayers" are the only people analyzing this trek from a factual basis. Many don't like that. Many feel nothing negative should ever be said. The problem with that is, as in this case, it ignores reality and silences the truth.