All of this stuff sounds different, and the sonic characters of competing models don’t necessarily "converge" towards similarity as you move price up. In fact, sometimes it seems like the opposite effect - higher end models can display more "personality" of whatever the designer / brand intended.
We also have difference preferences, and speakers effect different room interactions.
Higher prices implies higher budget, which allows more material, more sophisticated materials, and more complex designs. Sometimes those things lead to better sound, and sometimes they don’t.
If you liked the smaller speaker in this case, then maybe it’s part of a pattern where you prefer a more "coherent" sound (point source, panel, or line array). In that case, increasingly large boxes with multiple drivers are probably not the right pursuit vector. Or maybe it was something else entirely :) Sometimes the wiring in a system or crossover is even wrong!
On the other side you’ll have the ASR / flat-measurements folks say this happens (different sound) because it’s all produced distortion in varying types and amounts. And there’s truth to that. But the problem is that most of the "measures flat" gear they love sounds awful to me.
And to answer the question directly - yes I have sometimes preferred the lower model in a speaker line to a higher model. Pretty much any modern 12" Tannoy, I’ve preferred the lower 10" model to it. But then I like some of the 15" models above that. Don’t know why! Also, I have yet to have a really great listening experience with one of those monstrous huge box, multi-driver, > $100K super speakers from the likes of Focal / Von Schweikert / Wilson / Acora etc. I've had better experiences with the smaller models in each of those brands.

