I would check the wiring on the drive transformer, the jumper should be from H1 to H3, and H2 to H4 for 230VAC in, 115 VAC out. Power is in is connected to H1 and H4, i.e. the coils are in parallel for 230VAC operation. You could check the output with a voltmeter with the output fuse removed. You could run the drive direct from 115 VAC, but there is some potential benefit of using the transformer which isolates the drive and limits the current. As mentioned, I do not see the need to power the drive transformer through a contactor/relay. I do not see the benefit to have it switched on by a contactor that is triggered by the VFD relay.
I tried to find a schematic for this mill, but the manual only describes the DC drive. Some of the wiring, like to the motor looks a bit crispy and may need replacing, in particular if it is being hooked up to the VFD output.