It's interesting to me that the word is so often used to describe Jesus' reaction to the excluded, the marginalized and the alienated. See, legalism wasn't the big issue in first century Judaism. The average first century Jewish person understood perfectly well that it was God's grace which saved him/her, not strict adherence to Torah. The issue was the exclusionary use of Torah, the fact that it was widely viewed as the identity badge necessary to be recognized as a follower of YHWH, one who would be included in his kingdom when he ended the exile and established it on earth. Paul will spend his entire later career arguing against this very idea, that the Jewish Christians have some advantage over the Gentile Christians because the Jews were the recipients of Torah (see Romans 8-10). In other words, the problem wasn't legalism, it was exclusivity, which in God's eyes was an issue of injustice.
So, back to Luke. At first glance, it seems like Jesus just feels bad for a widow who's lost her only son. It's certainly not less than that, but it's much more. Left without any male relations, a woman would have been left without recourse in first century Jewish culture. She would have been pushed to the outside, left to die by her own people very much like the Jew in the story of the Good Samaritan. By raising her son, Jesus restores her as well. This healing is at the same time an act of inclusive justice.
The healing stories aren't just nice tales about what a great miracle-worker Jesus was. They aren't there simply to reinforce his divinity or prop up his Messiahship. That's part of it, but only part. They are violent attacks against systemic injustice and exclusivity that marginalizes those God came to rescue to begin with. They are acts of sabotage, designed to bring the ruler of this world to heel. They are the underground railroad, through which Jesus smuggles the left-out into his kingdom.
The intolerable are not simply tolerated; they are loved in transforming ways by the Messiah, Jesus.