Aha!

I think I'm finally onto something. Here and here are a couple of interviews with Handler. Note two things he says:

Handler has also said that the books follow the great Jewish traditions:
The Baudelaire orphans behave well and bravely because it's the right thing to
do, not because it will get them ahead. "Judaism doesn't really promise any
reward, they just emphasize that good behavior is more or less its own reward, "
he said.

And:

You've been quoted as saying that your books 'stem from great Jewish traditions' - which traditions in particular?

Guilt, the importance of morality in one's behavior rather than in one's heart, a belief that many large institutions will treat one poorly and the search for meaning in rhetorical details and food.

This is very similar to something Michael Medved said recently about why Jewish culture is actually better for the renewal of society than Christianity:

How have liberals done such a good job of associating themselves with virtue?

MEDVED: By emphasizing good intentions while ignoring bad results.
This is one of those things where Judaism actually fits better to conservatism
than Christianity, because one of the teachings of Judaism is that performing
the commandment counts more than your intentions. Judaism believes in changing
the heart by changing your actions. Christianity tends to emphasize changing
your actions by changing your heart. In this sense, serious Judaism sets you up
very well to reject the liberal scam that we are wonderful and nice people not
because we actually help anyone, but because we want to help.

and:

Real Judaism has two central thrusts: One is replicating in your life the values
and practices that your grandparents honored. The other is taming human nature
with law, emphasizing doing your duty rather than following your heart. Both of
these will lead you to conservative conclusions, which is why Jewish liberals
who try to remain religious have to go through all kinds of pretzel-like
philosophical and ideological contortions.

I find this fascinating and perhaps it explains something about my uneasiness.

First of all, I really don't think all Christianity is simply a matter of the heart over the law. At least Catholicism has a much more complicated version of the relationship between the two. In other words, the fact that all is grace and right action flows from a transformation of the heart does not let us off the hook as far as living according to God's law. We are still judged by our deeds and darned well better make sure our deeds correspond to God's will. But, when they don't, and they often don't we have recourse to God's mercy.

Second, Medved seems to think secularized Jews are a big problem. Is there anything to Handler's statement that:

I was raised largely in the Reform movement with a few sidetrips into
the Conservative movement when deemed necessary. I would call myself a
cultural Jew for the simple reason that I'm not a religious anything.

Does domething of that bleed into his writing?