Does the duantless title allow Oicunn to ram a ship, cuase the damage, then boost and then get the stress? Or does he need to end his activation touching the ship for them to take the damage?

The damage is dished out immediately after the maneuver.

He can theoretically boost, tho he would have to clear whatever he rammed for a successful boost (he can't cause ram damage with this boost).

Then he receives the stress.

Daredevil and inspiring recruit is better.

Daredevil inspiring recruit, Intel agent and boshek is best