Yeah, going from no saw to yes saw is obviously the biggest move. Beyond that, going from an aluminum table jobsite saw to a beat-up but cast-iron "motor-hanger" import contractor saw (I spruced it up and added a fence roughly equivalent to the ones that came on the Ridgid R4512) was a bigger jump than when I was using the makerspace's big 3hp and 5hp cabinet saws with Biesemeyers. For me, that first jump from jobsite to contractor is the move where the value-add is worth it and you're not too deep into diminishing returns.
I'm currently on the spiritual successor (and possibly literal, depending on which factory in Taiwan they came from) of my "project" saw, a Sawstop Contractor saw. I think it's the only one on the market that still has an outrigger motor, but I see no need to spend the money to upgrade any farther. The weight, the ability to adjust back into square, the induction motor (versus universal), the standard 27" depth and 3/4" miter slots, and the ease of adding supprt and fence capacity. Even staying out of the Sawstop argument, you get all of that with the jump to a Delta 36-725, or even an old Craftsman 113 (with SOME sort of upgraded fence).