About Rolan departing to save Cal and Lia alone. The feeling of guilt and inadequacy primarily drives it.
Ok, let me explain how I see it.
Let's omit all the game mechanics (aka, this little story arc starts when and only when your party arrives at Last Light Inn and talks to him. Who knows how many days have passed, blah-blah).
In terms of the story itself, let's agree that AT LEAST a couple of days passed between the kidnapping and the party arriving at LLI.
All this time, Rolan is in the inn and dulls down his grief with wine.
The reason he didn't attempt to go and save them earlier, in my opinion, can be attributed to him being sensible. He says it himself, "I know when I am outmatched."
And he is right. If he goes there alone - he will die. If not because of the curse, then by the cultists' swords. He doesn't have allies or a magical squid that protects him. Even the Harpers can't reach the MRT until they have the lantern. So, he accepts the reality.
But then, the party shows up. And the feeling of guilt and inadequacy consume him with new force.
You tell him that it was good of him that he shielded the children - he berates himself for not protecting Cal and Lia, too.
You suggest saving his siblings - and it destroys Rolan. Why can't HE do this? WHY is HE incapable of doing this?
Those feelings are so all-consuming that he throws all common sense aside. It hurts him so maddeningly bad that he is ready to die.
It doesn't take away from his bravery and skill. But it does show how fractured his mental state is, and it is fucking unbearable, honestly.
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