Poor Dick, always the sidekick, always living in Batman's shadow. I'm no help, I admit, as I'll be starting off chatting about Nightwing by talking about Batman. I'm sure I'll be forgiven, though, half of the Internet is afflicted by the same need to talk about Batman.
Batman has, I think, the largest host of villains in the DC Universe. Or at the very least, he has the largest group of known villains. This is in large part due to his constant re-emergence in the popular culture, his TV shows and movies, but I suspect it is also due to the higher quality of villain Bats encounters. By higher quality, I mean that there is a sort of twisted bond between Batman and his rogues which leads to more engaging storytelling. As I've said before, Batman villains all are dark reflections of some aspect of Batman. Joker is a different reaction to One Bad Day, Penguin is the Son of Privilege Denied Happiness, Catwoman is Idle Ability, Scarecrow is Fear Internalized, and so on.
There is a second tier to Batman villains as well. These characters are also reflections of Batman, but rather than twist some internal character trait or What If of the character, they're just fit dudes in fancy suits, usually with an animal theme of their own. Killer Moth, Catman, Copperhead, etc. Their What If concept is nothing like "What if Bruce Wayne let his fear take hold of him and rule his life?" but instead more akin to "What if Batman was a bad guy? Also, moths." These guys tend to be just interesting enough for a battle here and there, but not so much as recurring threats. Looking over the list of Batman villains on wikipedia it's easy to spot these also-rans. Just look for the "And then Neron gave them powers" - if your characters is so meh that it takes a satanic stand-in to jazz it up, it's already too late.
And in addition to all the villains who are in some part Batman, we have a host of heroes who want to be Batman as well. Batman, Inc is just the latest example of this trend, but the Batmen of All Nations concept goes way, way back. Hell, even Green Arrow and the first Blue Beetle are rich dudes in suits fighting crime for some reason (this also helps explain why I went with a fixie-riding lower-tech Arrow and the Jaime Reyes Beetle).
All this before we even get to the Elseworld versions (Owlman, Gaslight, Egyptian, Vampire, Beyond, etc).
Into this over-saturation of bats walks Dick Grayson, the one guy who, when it comes right down to it, has the biggest claim to be a Bat-knockoff. But by the time he does so, assuming the mantle of Nightwing, it's too late. He's like number 63 in an ongoing series. Batman himself doesn't help much. At least Flash and Green Lantern had the good sense to die/retire often enough to give others a crack at the job. But not Bats! He just gets shoved into a Lazarus Pit every so often in order to stay fighting trim and then just keeps on trucking. On those rare occasions when he's actually out of action, poor Dick still doesn't get a break. Instead, we have Battles For The Cowl and jerks with fireswords running around.
And when Dick does get to be the one real true Batman, he has to do so with Bruce Wayne's actual son as his Robin. Talk about a ticking clock.
So it's no wonder Nightwing is so pissed off. For Nightwing to function as a crime fighter, he has to remain in Batman's shadow. Funding requirements alone require that Dick not piss off Bruce too much. Kevlar-weave body suits and bird shaped boomerangs don't just grow on trees and it's not like Dick spent a whole lot of time learning the ins and outs of investing. Hell, Nightwing doesn't really even have his own villains, does he? He's got a lot of leftovers from his time as Robin, both under the Bat's wing and as a member of Teen Titans, but nobody to call his own. I guess this a common problem of all sidekicks (although Roy Harper has his own nemesis, smack), but as the greatest of the DC sidekicks, you'd expect Dick Grayson to come out with at least one.
It is this quest for legitimacy that we'll be focusing on in Nightwing (#28/54). In the Drewniverse, Batman has already had the same sort of impact he's had in the conventional setting. There is a host of dudes out there running around with the "Driven Expert Mystery Man" motif attempting to be the Batmen of Crime. So rather than join the Teen Titans (No way would Terrific let a Bat-plant into his Titans anyhow), our Dick will spend his gap year hunting them all down and beating the crap out of them.
This will be a bit of a twist on Batman's normal MO. Rather than stopping the crime, Nightwing will be more focused on stopping the person. That a crime is stopped as well will be a happy side effect. Nightwing doesn't care so much that Killer Moth is escorting a shipment of illegal weapons from Metropolis to Star City. He just wants to bust Moth. And will do so. On a train. Speeding through the mountains. With his fists.
By beating these evil Batman analogs, Dick will be in effect proving himself as being more than Batman's shadow. Each one he takes down is a statement - "Look, I'm better than (this) Batman." Our Dick does not hate Bruce or anything, he just hates that his growth in his chosen vocation is stunted by his prior career as Robin. Bruce (who is still funding this quest, remember), gets someone out there defending, in effect, his brand identity. It's hard for a man who is dressed like a bat to strike fear into criminals if they are used to working with guys dressed as moths or snakes or cats or whatever. He also sees this world-spanning adventure as being akin to the sojourn he took before he even put on the cowl. Remember that Bruce walked the Earth for awhile before becoming Batman. While he sent the young Dick Grayson around the world to train with similar masters, the whole thing was planned. It was a packaged coach tour of Europe compared to a backpacking wander. He sees it as important for Dick's development. Always with a plan, that Batman (also, if you consider that his Outsiders exist in part to take down Justice Leaguers, wouldn't he also plan for someone to be able to take him down should the need arise?).
From the perspective of someone who is rebooting a universe full of familiar and obscure characters, Nightwing's quest also has the advantage of providing an easy path to introducing the wealth of minor villains that populate the world. Of course, the quest will grow over time as Nightwing starts to pick out common threads raveled around his defeated foes. This will lead to bigger and better enemies (Deadshot, Deathstroke) as well as introducing the League of Shadows (I prefer Shadows over Assassins) as a force within the Drewniverse. The goal here is to build Dick Grayson/Nightwing up as his own character, Robin no more.