I for one do not care for getting "better" gear as much as I used to do when I ran a 25 man guild. I always wanted a full matching set asap. Not specifically because it was a better set, but because I wouldn't look like a clown anymore.
Now I never (unless I want to) look like a clown. Even during leveling I transmogged my gear everytime I got something new. Sometimes I didn't use an upgrade if it was minor because I couldn't be arsed moving back to the transmogguy.
So yes Transmog helps you not care that much if you have pro gear or not. That said, I still want upgrades
it makes "grinding" that much easier.