The reason I ask that is that it has been suggested to me that one ought not upgrade to 3 before one has had a "big" win.

I guess in my case, that would be winning one of the local state road races, or one of the regional big crits. Maybe Cat 4. Maybe 35 4/5. I've won three weeknight crits in 2 seasons.

I personally feel like winning a "big" race as a Cat 4 doesn't matter much to me, so I will probably upgrade before I even attempt a "big" race. just so I can start doing the local A crits on weeknights.

But maybe I would regret that. [hand wringing trigger alert].

Also as a master's racer, I think category tends to matter a bit less. As a Cat 4, you can still race the 35 4/5 or the 40+. There's more flexibility. And the incentive to go from 3 to 2 is pretty minor I think. My club has incentives for upgrades. The shop discount goes up for every upgrade. [category discussion ad nauseum trigger alert]