Souma is in the Silent Assassin tournament but he is also (once you get past his outer shell) kind of a complete softie. It's been a long time since he was in a fair fight situation. Would you mind if they run into each other?

At home Souma was part of a village of warriors and they did a lot of wargames and training exercises as well as the real thing. If he noticed Itaru dragging or like seeming tired while hiding and trying to find a mark, I think Souma would approach and maybe offer something to drink and eat, etc. Maybe point out a good person to go after. He'd know he was risking being attacked, but he might be more motivated to help someone in need.