I have reproduced a situation where the train schedule forgets destination after leaving train builder.
The train is left in Automatic but the destination depot play button turns from enabled to disabled (not unreachable) after the last carrage passes the train builder.
If I leave the train alone it will carry on with momentum and crash into other trains. To fix the issue I have to retarget the destination depot by pressing play.
I can reproduce the issue by removing all the trains in the depot and setting the depot to request more than one train.
The trains sometimes stack correctly or sometimes go into the bottom bay (not a depot) one after another and crash into each other.
I believe the issue is that the train is driving to the depot, and resetting the schedule before it arrives at the depot might have this behaviour, I will look into this