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From there you just need both his passive and his crit and that might get you to 300 through the compounding effect of all of that. Any form of attack up will also help because that'll flatly add large quantities to the end damage. Though that's just theory crafting I'm sure someone else here has properly tested it.
Build up his coins to 4
Use his skill 3
Crit on both coins
???
Profit
Needless to say that you need uptie 4.
Make sure you have other members on your team that can inflict bleed, preferably bleed count (Hook Hong Lu, Kurokumo Ryoshu, etc). Greg can get unjust enrichment if he roll heads when attacking an enemy with bleed. Unjust enrichment boosts dmg of the last coin on his S3 by (25 x unjust enrichment)%, with the cap of unjust enrichment stacks being 4. So that should be a extra 100% if you max out unjust enrichment.
Greg also deals 100% extra dmg if you land a crit with the last coin on his S3, so spaming his S2 builds up more poise count and makes it more likely for him to crit.
Put him on the first slot on your team and he'll generally have priority of extra slots in focused encounters, letting him generate poise/count more easily.
Good active units include:
N Faust (bleed)
Kurokumo Ryoshu (bleed)
N Meursault/ R Meursault (bleed)
Hook Hong Lu (Bleed)
Good Passive units include:
Blade Lineage Yi Sang (poise)
Base Don Q (Pierce Dmg)
Kurokumo Ryoshu (Bleed)
Base Rodion (Dmg)
Los Mariachis Jefe Sincliar (Dmg)
Base/Blade Lineage Outis (Dmg)
If you are making a team dedicated for Gregor with some support, I would add at least KK Ryo, Hook Lu, and maybe N Faust to keep bleed high
For support I would go with whatever is left on the good passive list and use base Outis over BL Outis.
Here's a video of someone doing 257 dmg with Gregors S3 (skip to 4:30): https://www.youtube.com/watch?v=shNvgGLFkhU
No one mentions Rhino Meursault, the best bleed count inflicter in the game? Really?
Ryoshu's passive only works if Gregor uses his last bullet. Which I've never seen happening in dozens of battles I've used him.
You would need to intentionally stall the fight to make him use his last bullet, or go solo.