Maybe ? It's hard to figure out what they were thinking when every decision was stupid. They pretty much explain what you're saying on the minc law site
https://www.minclaw.com/guaranteed-content-removals-listing/
These guaranteed removals are what you're talking about. They offer a flat fee. I'd guess that's the majority of their business. But even then minc law knew it was a John Doe case, so they knew it was going to be complicated. I can't even imagine what resto was thinking.
My best guess is that he's never dealt with an anonymous entity before. They reference "cheater" sites
https://www.minclaw.com/cheater-websites-legal-how-do-they-affect-me/ , those probably have a corp or LLC at least. It would be similar to the Kiwifarms subpoena. He didn't include null as a defendant.
So he didn't really have a plan, and Resto's tech knowledge torpedoed any chance at a non quash resolution. Read the email exchange again, Brinton said that the IPs were cloudflare ips and the emails were fake. So the best formulation of a plan was that quasi would hand over real emails and end user ips. But quasi didn't require email verification, and resto doesn't know how a reverse proxy works. Cloudflare acts as the dmz for the internet traffic. So user-->cf server --> forum server. To the server, you just get cf traffic. They could have subpoenaed CF for the end user ips.
The last and biggest blunder is probably that Brinton didn't realize anyone would quash in California. He almost certainly didn't know about the cost shifting statute in CAL. though to quash the subpoena in California. Null didn't. No matter what you think about the state's politics, they don't fuck around with free speech laws.
So the tl/dr - I don't think he had a plan. The bully and settle tactic couldn't even be attempted because they wouldn't remove quasi as a defendant. Quasi's posted before that their entire negotiating tactic was "we get everything and you get nothing. You have no upside in settling". How can you negotiate, but offer nothing?