It took me nearly six months to get official (white in my case) plates after buying a new car. So I was using the temporary red plates during that period, and it was a pain. I never had any issues with the after-dark restriction, but did have some issues with the "driver's log" requirement.

I can't speak directly to your experiences but suspect that said "red-plated" vehicles may just be new and waiting for the proper plates, so they may be legal.

Driving, navigation and finding one's way around the silly traffic lay-out here can be challenging. Sometimes if I miss a turn it might take me 2 -3 Km, and another 30 minutes to get back to the proper spot.

Thailand doesn't really have "laws" in the sense that most might be used to; they don't even have a justice system, so I doubt Uber is "breaking any laws". That said, there are so many governmental and military-sponsored "organizations", "committees" and "panels", all with myriad "regulations", "rules" and "core values", that at any moment everyone is "breaking" at least one rule, so in that sense, Uber may be "guilty".