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Chuck sure did love writing about those Batboys. Here’s a 3-volume map of his lengthy stint on Nightwing.

Volume 1:

Nightwing 1–8
Nightwing Annual 1
Nightwing 9–18
Nightwing ½
Nightwing 19–22
Nightwing 24–25
Nightwing 1,000,000
Detective 1,000,000
Nightwing 26–29
Batman Annual 23

Volume 2:

Nightwing 30–35
Nightwing Secret Files & Origins
Nightwing 36–45
Birds of Prey 20
Nightwing 46
Birds of Prey 21
Nightwing 47
Action Comics 771
Nightwing 48–51

Volume 3:

Nightwing 80-Page Giant
Nightwing 52
Nightwing 54–59
Nightwing: Our Worlds at War
Nightwing 60–64
Nightwing: The Target
Batman: The 10-Cent Adventure
Nightwing 65–67
Batman 600 (minus the backups)
Nightwing 68–69
Batman 605
Nightwing 70

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Notes:
Batman Annual 23 is part of the JLApe annual crossover, but it’s basically a extended (and pretty fun!) Nightwing one-shot. This is where Blockbuster meets and takes in Grimm the gorilla, which plays a key role in the “Hunt for Oracle” crossover soon to follow.

Nightwing 23 is part of the “Brotherhood of the Fist” crossover & Nightwing 53 is part of the “Officer Down” crossover.

Action Comics 771 is where Nightwing (with Supes’ help) takes down Torque’s Intergang suppliers. Superman/Nightwing team-ups are always fun, and Chuck writes them both perfectly here. This is actually one of the best Nightwing issues he wrote, IMO.

I left in the beginning and conclusion of the Bruce Wayne: Murderer/Fugitive storyline so the Nightwing comics during that time made sense. Batman 600 portrays a key relationship change between Dick and Bruce, and with Scott McDaniel back on art duties, it fits right in. I think it definitely needs to be included, even if you leave out The 10-Cent Adventure & Batman 605.

Nightwing Annual 1 chronologically takes place before the entire series, but putting it first would be weird, so I just stuck with publication order. It’s also by Devin Grayson, not Dixon, and is completely standalone, so it could be removed if you really wanted, but it’s a good story and Greg Land seems to actually be drawing people instead of tracing them at this point in his career.