Full disclosure - I was already a Brooks fan before this book while my boss can't stand him, so keep that in mind. My wife and I saw him in person last year at a CT Forum event with Ralph Reed, Frank Rich and Margaret Carlsen. (Tonight, we're celebrating my birthday a month late and going to see Tom Friedman and Malcolm Gladwell.)
Regarding On Paradise Drive, it was much less even than Bobos in Paradise, his previous foray into social commentary. Bobos had a better unifying thesis and had better flow but the very best parts of Paradise Drive were so insightful and cutting and funny that I was repeatedly laughing loud out while reading it. And not little chuckles but full belly laughs. Here's a free copy of the rest of the original Patio Man essay. I stopped before Brooks described his wife Cindy - Realtor Mom- and their children Haley and Cody and their cul de sac friends Cory and Britney.
And yes, Chapter 1 opens in the urban core, with equally cutting commentary on the "urban hipster zone". So yes, read OPD.
With regard to his writing at the NYT, I don't think you give him enough credit. I don't think he's a token kneeejack conservative at all. Rather, he's been described as "a liberal's conservative." First of all, he is ideologically a conservative, but I think he wants the same things progressives want: social justice, educational and economic opportunity, etc, but he doesn't agree with big government approach as a means to that end. Second, he is actually a thinking conservative, meaning he doesn't only drink the company KoolAid. He'll call out both sides when appropriate and he'll reacch across the aisle and give credit when credit is due.
Consider his Sept 8 column on Katrina:
Supporting mixed income integration and giving credit to a Clinton era program doesn't sound like a "defender of all things traditional, Republican, and conservative. " to me, but as I said, I was already a fan. Now as urbanists, we may not like the idea that only the suburbs can provide middle class values, but when I read that column, I think he's showing some rather progressive ideas filtered through language that conservatives can relate to. Ask yourself whether his message of high standards and achievement is very different from what Barack Obama is selling - I don't think it is.
Anywho, back to work.