It hasn't been in a similar patern but ever since the update of today I haven't been able to complete a service. It keeps eventually saying that the game has crashed and will close. Thus far it has happened on the Long Island Railroad route, East Coastway and Hamburg-Lübeck.
I was on Sherman Hill free roaming around and looking at the map and it began crashing my pc. I restarted the PC and it happened again today 3 more times. So instead of running the TSW2 program I went on Youtube and while watching a video my PC crashed again without TSW2 running. So figuring that maybe the Steam app that was running in the background, I went into my PC Windows task manager program and under processes I disabled the Steam app from starting up automatically on my PC. I then I shut the PC down, and restarted the PC again but this time without the Steam app running in the background. I went back on Youtube again but have no crashes yet after doing this disable on Steam app. We will see if the Steam app update recently is the problem causing the crashes.
If you get the "Retry was NOT successful" error code, verify your game files. The Update might corrupted your game integrity.
File verify is something that I do after every up date. Just remember that you have to load the game and exit it prior to doing the verify. This allows the new files to be loaded into the game.