Let's take the achievement where you operate any rail vehicle for 10,000 mi. I'll do one service and it will not track, but then I will do another service and it will. There are many others like it
The ones I am making process in are tracking fine. No issues. There are some unobtainable achievements at the moment, though like the DRA: Dresden Commuter one.
Yes, but it's not just TSW. I have a couple of "win a rally at xx location" achievements in WRC10 that didn't pop up when they completed so it looks like a regional XBL thing.