In the case of the second drop of preserved collection, we're just going to have to wait on it being fixed unfortunately. With your TSW2020 Tees Valley Line, you need to reacquire the license via the Xbox Store by redownloading it, although because it is already on your HDD, this should just be pretty much instantaneous. However, once you boot up TSW2 again, it will uninstall the license from all preserved collection routes on TSW2020, because Dovetail...
Should it make a difference if we still have TSW 2020 installed or not? I uninstalled 2020 some time ago, as didn't see the point in having it sitting there is I wasn't going to use it.