I feel like several of the other books make it quite clear that invincible, well-meaning good guys can cause a lot of pain. Sometimes it works, sometimes they convince themselves that it was worth it, because clearly their ideology is the better one, sometimes they are terribly sorry for what they did. In any case it will hurt if you are on the wrong end of their meddling. And most of their population doesn't care or even notice, so happy or unhappy are they in their utopia. Really, tons of material to draw parallels from, to all sorts of things in our lives.

I'd put Look to Windward in the "best of" category. It addresses with the issue by introducing a character who has been personally, very poignantly affected by the Culture's meddling, and seeks revenge for it, a bit like a reverse Use of Weapons. It's also the only book to directly reference the events of Consider Phlebas.

I also liked how Matter described a very-low-on-the-civilizational-ladder (literally: It's a located on the lower level of a "shell world", an artificial planetoid constructed of concentric layers of habitation, each home to a different civilization) society whose players discover the Culture and ultimately seek to improve on themselves, while the book concurrently illustrates the other civilizations' underhanded attempts at playing the Culture.

Minor nitpick regarding Consider Phlebas: The Idiran Empire are militarily vastly superior to the Culture at the outset of the war.

Fun fact: "Consider phlebas" and "Look to windward" are both phrases appearing in T S Eliot's poem "The Wasteland".

They're the only two titles drawn from the poem, so I find it particularly interesting that you mentioned the way that they're more directly referential than other works. Makes me think I should try a closer reading of both.

Yes, it's a "sequel" of sorts — in the weakest possible sense — to Consider Phlebas, so it's not an accident that he used another line from the same poem.