In "port configuration" window, if the port is disabled by unchecking the "Enable" check box, and checked again, VTS will crash if already composed services are resent. The necessity of this operation is to run other BACnet applications in the same PC, throughout the exercise. The resulting inconvenience of this bug is, we have to re-compose all the BACnet services repeatedly.
The crash occurs because the Send dialog keep a pointer to a Port object. When the port is disabled, the object becomes invalid. Fixing this would require significant refactoring of the Send logic.
Since your use case (disabling and re-enabling a port within a session) is not typical, this is unlikely to be fixed unless you submit a patch to do so.
In the mean time, you might consider using VTS scripts instead of the Send dialogs. While they take a bit more effort to construct, scripts have the advantage that they can be re-used between different executions of VTS.