What's currently happening to Sunless (Ariel's game) is abso-fuckin-lutely improbable.
Not that things happening to him generally in the plot are probabilistically reasonable in any way; but it was lampshaded in the best possible way; this boy is Fated, he's both blessed beyond reason and cursed beyond reason, probability looked his way once and decided it has an urgent business elsewhere; and even after he stopped being Fated, many of the improbable things happening to Sunless was explainable as consequences of things that happened when he was Fated still.
Now however, he entered an entirely new arc where he really SHOULDN'T have it THIS easy. He's heavily nerfed. He's facing enemies more powerful than ever. It shouldn't go this easy for him.
(I mean, I know that Doylist explanation is that he WILL get that particular boon no matter what and also if he dies his un-resurrectable companion dies and this level of additional guilt would mess up the themes and so on. But. Let's look at Watsonian reasoning at the moment)
All of this can be explained, if we assume that all of his current opponents were handpicked to be defeatable particularly by Sunless.
Which makes sense, because ultimately, they all were indeed handpicked by Weaver at some point.
But also doesn't make sense, because, while Weaver was Demon of Fate, Sunless is currently not touching strings of Fate at all, as he literally physically represents the hole tore apart in the tapestry of Fate; his presence might be at best deduced from unexplainable lack thereof; he should be undetectable and uncontrollable.
In order to bridge all this mess, I'm choosing to believe that current arc is proof of ultimate mastery on Weaver's part: that Weaver actually managed to provide controllable environment yielding the expected result through the uncontrollable and undetectable medium.
A sorcerous equivalent of writing (engineering) a pre-programmed aleatory concerto on a theremin and a colony of squirrels.