I recently got an Xbox Series X. I already own several TSW2 trains & routes on STEAM. My main question is, now that TSW3 is coming out, is it possible to transfer my TSW2/TSW3 collection from STEAM to Xbox, or will I need to re-purchase the entire collection for Xbox when TSW3 comes out? Also, will TSW3 overwrite TSW2 on Steam or is it a completely separate game?
You will have to buy it again if changing to a different ecosystem. TSW3 will be playable on Xbox and PC if you get it on the Microsoft Store.
Steam considers them different games. You can have both installed at the same time and, for example, play the old version of SEHS in TSW2 and immediately after start TSW3 and play the extended version of SEHS.