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Issue #19 is the first tie-in to a Batman event, Cataclysm. It's pretty self contained though. Mostly just Dick trying to save people trapped by the earthquake. I think it's sweet that the kid calls him Batman and he just rolls with it.
Dick has a truly eclectic group of neighbors. Clancy is of course a great character, but now there's also John Law (the original Tarantula), Tad Ryerstad in the neighborhood (Nite-Wing), and Amygdala. The development of Dick's civilian supporting cast is pretty good.
There's also another meaningful appearance of Oracle, where she talks some sense into Dick about Bruce seeing him as an equal. It's also the first hint towards there being a potential romance between them (this is issue #16). Peak DickBabs is definitely the late 90s imo.
There are so many great bits of characterization that get left out of fanon, because fanon only focuses on the Bat-family crossovers and interactions between the boys.
Dick is a total gear-head, a capable mechanic and engineer. His car is designed to blend in to Blüdhaven.
After snapping at Bruce, Dick reflects and feels bad for how he acted. I like that he still has a blue/gold suit, and his Robin suit, as well as a box full of extra escrima sticks. I also like his conversation with Alfred.
This culminates in Dick finally lashing out at Bruce and effectively sending him packing. Because neither of them are great at talking about their emotions.
This continues into the next issue, where Bruce and Dick are captured by a local mobster and have to escape. Bruce uses a new addition to his suit to get out first, and there isn't enough time to get Nightwing free.
Of course, Dick is able to get himself out anyways.
Dick's been making it on his own with money from the bar, but refuses to use Wayne money, so he doesn't have a proper lair set up, and hasn't been able to get a car yet. This is when he learns that he has a sizeable trust fund that Lucius Fox has taken care of for years.
The kid ends up getting hurt, because he was supposed to be stealing from people's homes for a local gang. Dick saves him, gets him to the hospital, and then gets him a job at the bar he works at. A happy ending for once.
Dick catches a small-time burglar in the act in his apartment. He's just a kid, and Dick lets him go (with the promise that he won't try anything like this again), and follows him to make sure he gets home safe. I like that he's always helping people, in and out of costume.