I watched Yojouhan Shinwa Taikei back in 2011. I was a noob and thought it was a masterpiece and the best thing ever. Recently, I rewatched it and came to realize that it was just the wannabe-elitist in me thinking this show is any good. It's basically the same as Sword Art Online, just the other end of the same shit-stick.
The story of this series is identical to Endless Eight from Suzumiya Haruhi S02. Only this time it is apparently meaningful and deep and provokes some thoughts in people. All I see is yet another teenage drama aimed for people who are lost in life, executed in style over substance manner so people who wouldn't like it could just be told they didn't get it.
When it comes to this being like SAO, instead of focusing on an overpowered gary-stu isekai jesus who gets all the bitches and is best at everything he does, Tatami Galaxy focuses on a man who is practicing escapism in a timeloop and dwelling on self-pity. The main difference is the comfort which has changed from "it's all good now" to "pretty much everyone else fucked it up too." Same shit-stick, same level of escapism, other end.
The characters are the worst part of this show. They are such an empty shells it's almost as if the viewer is supposed to put their own personality and buddies + high school crush in these shells and act like this is me. This is so me. Just like Kirito and his harem.
Back in 2011, I thought Yuusa Masaki was god. A gift to the anime industry. After seeing everything he has ever done, I can only call him a try-hard attempt of being the next Satoshi Kon. So try-hard even Netflix wanted to hire the guy. Speak of mainstream appeal. Also, I am pretty sure this series was created for western weebs in purpose of trolling. Why else would a male main character be called Watashi instead of Boku.
I recommend Yojouhan Shinwa Taikei to 15-20 year old audience, this will help you feel less shit about your past mistakes and deal with them. Make sure to never rewatch this, tho, you will/might only come to see what I am now seeing.