I still don’t really know what the difference is between the two,whether ones Sim or not, what the technical differences are
One is built using the a modern version of the Unreal engine, the other with an over 10 year old development environment. Pretty much sums up the major technical differences.
From a simulative point of view, there is not so much difference in the base game. For TS there are more "advanced" routes and locos, where more aspects of physics, systems, etc. are simulated. That's because for TSW there are no dev tools available (only a basic scenario planner and a livery editor). Also, TSW simulates dynamic adhesion. From a graphics point of view, TSW runs on a modern engine (even if badly used by the devs). TS is 10 years old basically.
Maybe this will help out with TSW2 you have more physical interaction with the rolling stock and locomotives. You can actually walk around the routes. None of this is possible in TS2020.