I've rewatched the entirety of the Haruhi Suzumiya series a number of times, and each time I always watch the entire Endless 8 arc. I've seen it 3 times now, in its entirety. Every time I feel that it is worth it, and in this review I'll talk about why.
One thing I appreciate about this series as a whole is how it does not pander to the audience. Rather, it often frustrates the hell out of the audience. Whether this comes in the form of an extremely complicated chronology with multiple watch orders, a buzzword-heavy unintelligible pseudoscientific explanation of something crucial to the plot, 10 minute scene of Yuki reading in the clubroom with only background noise, a blatantly obvious time paradox that is never addressed, an 8 episode groundhog day loop, etc... These things can not be called pandering--they literally frustrate viewers. But this frustration is an intentional effect of parodying sci-fi and slice of life tropes to such a degree that it almost becomes tongue-in-cheek, as if critiquing those genres, and poking at their flaws. The Endless 8 arc is very much within the ethos of the series for that reason.
Yet, it was still a hugely ambitious and bold move. There's been nothing quite like Endless 8 before and there will be nothing like it again. It was an incredible unique experiment that was extremely risky and unlikely to pay out. There are various theories as to why they did it--maybe Disappearance was going to be covered in S2 and they scrapped it last minute to make it into a movie, as some say. As far as I can find, there is no evidence of this. In my opinion, it feels like a passion project. If you watch every episode, you notice that every episode is goddamn beautiful from every angle--art, music, voice acting, cinematography, etc. A LOT of effort was put into this experiment. Enough that it's very clear this was not some budget issue, production problem, laziness, etc.
Now, why did I enjoy it?
--Endless Eight begs the viewer to try to crack the mystery of what the team needs to do to break free from the loop. After all, "There must've been a hint in something Haruhi said!" KyoAni drops tons of red herrings, none of which pan out, frustratingly enough. When I watched it in 2009, I had my theories that maybe Haruhi was waiting for Kyon to ask her out on a date. I can just see Haruhi thinking, deep down, "no summer would be complete without a tense romantic encounter!" or something like that. Alas, it was much simpler than that. It was NOT anticlimactic though. It was certainly a huge payoff, but the simplicity of the solution definitely was frustrating as someone who had been tracking various motifs and hints throughout the arc, and hoping there would be some solution that elegantly ties them together, and maybe one that develops that Kyon x Haruhi relationship... But no, that would not be in the spirit of the show, to give the viewers that satisfaction.
--The subtle developments throughout the arc were satisfying. Of course there is quite a bit of development from episode 1 to 2, but later episodes have development as well. Something as simple as Kyon's deja vu being so strong that he could remember the exact sentence Haruhi was about to say, and say it in his head in the same exact tone of voice that she had. Or Kyon receiving the initial phone call from Haruhi and responding "Come on my bike, right?" This might not seem like a serious plot development, but I LOVED these moments.
--Watching from Yuki's perspective and trying to understand her psychology is interesting. Many people have thought "man Yuki must be so bored." This is an incorrect analysis... Yuki is extremely, extremely overstimulated, by having to loop DAY IN DAY OUT a hectic summer full of events in which she has no choice but to participate. We all know Yuki's preferred level of stimulation is to sit quietly and read a book. This is something she isn't able to do for 595 years straight because she's too busy with daily summer antics. During my first and second watch, I thought Yuki buying the mask was an attempt to stave off boredom in her own way. Now, I think it was her way of "participating" in the Bon festival in the way requiring the least energy, to maintain as much peace as she could... Sometimes she wears the mask over her face, sometimes over the side of her head to block her ear. Either way, it serves as something to block and lessen stimulation. Anyways, the theory about Yuki's mental state during the arc is more or less proved by the last minute of Endless Eight VIII, in which she misses a day of school, and Kyon guesses it is is because she needed a break to sit quietly at home.
--The delayed gratification and payoff of the end was extremely satisfying. The longer the grind, the better the payoff. If it was only a 2 episode arc it would not be nearly as satisfying, and that's why I feel that viewers who just watched the first and last episode of the arc are missing out.
To the many viewers who did not enjoy this arc--maybe it just wasn't for you, but also consider that maybe you weren't trying hard enough. Think of a mystery novel--in many cases, the effort you put into it results in way more enjoyment. Because you are analyzing everything, trying to crack the mystery. NOT just passively letting it all wash over you. Everyone is entitled to their own opinion of course, but I do hold this arc in fairly high regard and think of it as a great addition to a great series.