Oooooh, where do I begin? I fell in love with the series (and remember the horror and garbage that was 2013 DR fandom) around 2013. Going into it from Umineko is actually ill-preparing yourself, since Chunsoft really loves to spit in the face of Knox and Van Dine (especially considering how some trials aren’t solvable with the clues presented, and most of the twists, while some are hinted at if you look carefully, usually have little hinted at in the game).
One thing I love about the fandom is how brilliantly it weaves the pop culture references into itself without it being obnoxious. Leon in the first game is a full reference to Sid Savage of the Sex Pistols down to murdering Maizono in the shower, Ibuki in the second game is a walking K-On reference, and Sonia in the second game is a Nirvana reference from the emblem on her uniform to her last name to the name of her country. There are also many numerous JoJo’s Bizarre Adventure references weaved in that a friend of mine who loves JoJo missed them the first time (Mondo Oowada and his brother are a reference to the protagonist of Part 4 down to the hair, CRAZY DIAMONDS, and their names making up Diamond, the pose Junko uses with her hand over her face is a reference to the one and only Dio Brando and she uses his catchphrase “MUDA MUDA MUDA” during the Machine Battle Talk, Nagi’s first scene has him saying “I’m not a Stand user”, and there’s one JoJo reference in the second game). There’s the infamous Titty Typhoon skyline which I’ve heard is a reference to the movie From Dusk til Dawn. There are so many references worked in, and that’s just the tip of the iceberg.
The characters really shine, and for most of them, the characterization comes in the Free Time Events. It works well for a story that focuses more on the story, and you have the chance to replay chapters to focus on the FTEs. The characters are memorable to the point people forget the story.
My favorites of the series are SDR2, Another Episode, and Zero (plus the IF game). SDR2 to me has the most likable characters (and Hinata is a truly relatable protagonist with being the talentless snarky but caring guy he is). Another Episode introduced the first playable female characters and to me, was the first game to not sugar coat the awful things that happened to the characters, especially with the back stories of the Warriors of Hope. Zero is an absolutely required novel set that sets up a lot of things for SDR2 that may have come out of nowhere like the Reserve Course and Izuru Kamukura (and it introduces the really under appreciated Matsuda, Ryouko, and Gives some love for Mukuro). If was a story put in with SDR2 that the player could get after beating the main game, and it is an alternate idea where Naegi regains his memories in DR1 during chapter 1 and prevents Mukuro Ikusaba’s death, leading to a divide between the Despair sisters (and it’s where Ikusaba’s crush on Naegi is confirmed). I’m somewhat watching the DR3 anime and to be honest, I thought I’d hate Future Arc, but they’re going in a wiser direction than Despair Arc. (Seriously, poor Hinata got all his screen time stolen and Nanami is only vaguely like her game self, what about the other kids, Kodaka?! At least Future Arc is gonna borrow hard from AE and Hagakure is most likely gonna live, please let the family people reunite!)
Perhaps the thing I don’t like about it is that a lot of the fanservice, particularly with Tsumiki and Kotoko, is extremely misguided (especially since with Kotoko, getting stripped down is cringe-worthy with her being a kid who was also molested by adults). And I really don’t care for the Fujoshi of the fandom who reduce characters to an OOC version of themselves for gay porn and hate on female characters like Tsumiki who have more likely chances of ending up with the male characters due to better chemistry. Then again, the DR fandom is notorious for viewing a Japanese series in a solely Western lens (ala Chihiro gender arguments), so there are idiots out there who ignore anything canon and insist their interpretation is right. But once you avoid those people, you can enjoy the series.