Good luck. I'm rarely so absolute but Free Roam seems to have really been very minimal in priorities ever since it first launched, which is strange to me considering how much value it can add to every single addon ever for the right kind of player. Regardless it seems that having trains correctly appear there as an option isn't a fix that's linked to Free Roam so much as it is linked to the route or addon of origin itself, meaning DTG would have to go back to those routes to fix it and that is something they seem to very rarely do for any route over a year or so old.
There is NO true Free Roam mode. The "Free Roam" mode works like this: Choose starting and ending stations. Place a train on the track. Drive the train from starting station to ending station. Changing ends of train may or may not work. Train may run on wrong track - left track instead of right track. If there is true Free Roam mode, you could drive trains anywhere on the route and set track switches.