OK, now that you have determined that DOL is possible, you need to know that NO, it is NOT necessary to isolate the soft starter from the line or load when the bypass is energized. There is no problem with line or load power being in contact with the soft starter terminals when the bypass is energized, in fact most soft starters have bypass contactors included now anyway. the bypass acts as a simple power shunt around the SCRs, providing a path of least resistance for the motor power.
The only important thing to remember is that if the soft starter was providing solid state overload protection and it goes down, so does the overload protection. So your DOL bypass must be a complete starter (contactor + overload relay) not just a DOL sized contactor.
What most people do in this situation is that they have a selector switch for the contactor control circuit. In "Normal" operation, the contactor is controlled by the soft starter at-speed contact and the soft starter is providing overload protection, so the separate OL relay aux. contact is not in the contactor control circuit in order to avoid confusion as to which device has tripped. In "Manual Bypass" operation, the selector switch places the contactor control directly in the manual start-stop circuit and adds in the OL relay aux. contact to drop it out in case of an overload.
If by chance your soft starter never had OL protection or it is some low cost system that you want to override anyway, then get a good quality solid state OL relay and just place it down stream of the tie point of both controllers so that the motor power is always going through the same OL relay.