I stand by my position that it's quite hard to know in advance what is going to happen with a game like that these days. Maybe a month before release you should have an idea, but at the point of debarkation, how would he know that this isn't going to be the latest quirky runaway success like Gone Home, Firewatch, To the Moon, 80 Days, Undertale, etc. I've only played half of those, and I haven't played this game, and it sounds like a key difference is the excruciating slowness of this game, but I dunno, it really doesn't seem obvious that it was going to bomb, especially as it crept along and won a bunch of prizes and massive news coverage.
To me, this is like some amateur boxer who somehow manages credibly to fight many rounds against a champion, only to take some hilarious, meme-worthy knock-out punch in the last round that makes him a laughingstock. Sure, it ends ridiculously, and maybe the guy was a goofball from the outset, but in the interim, he actually pulled off the remarkable feat of several rounds of impressive boxing. There are all sorts of games that fare way worse than WTWTLW has --
Kim by The Secret Games Company seems a decent point of comparison. Or, heck, The Long Journey Home (which has sold a few more copies, but has been out for months and steeply discounted, and had ~20 times the budget and put an entire wing of Daedelic out of business), or Sunless Skies, or that random Victorian New York RPG that came and went, or Bob Bates's Thaumistry, or Telepath Tactics, etc. And that's not even counting the endless shovelware out there.
It doesn't mean the meme-worthy knock-out punch isn't still funny, but I still think he achieved quite a lot along the way to being knocked out. Maybe part of the reaction is the feeling of relief that it didn't succeed, lest the world seem even more ridiculous.