> ============================
> Let us go, through certain half-deserted streets,
> The muttering retreats
> Of restless nights in one-night cheap hotels
> And sawdust restaurants with oyster-shells:
> Streets that follow like a tedious argument
> Of insidious intent
> To lead you to an overwhelming question...
> ========================

The ambiguity, if not intentional in writing, is certainly intentional in

However, I tend not to read it as the streets, but the arugment that leads
to the overwhelming question.

The streets reading does give you the easier text to follow - the more
literal move through the red light district, etc.

But the entire poem can be read as the "tedious argument of insidious
intent." It's a statement of his case - leading up to his question - only to
be answered with "That is not it at all."

The overwhelming question is what he's heading toward through the whole poem
- it's what the argument is supposed to get him to - but he gets caught in
his own argument and its digressions. The concern over how to even phrase
the argument becomes too much for him - and the overwhelming question shifts
to how to make the tedious argument - what will be the convincing words, and
does he even have it in him to say them. ("Shall I say, I have gone at dusk
through narrow streets...")

The second mention of "overwhelming question" comes only a few lines before
the last section break. ("Would it have been worth while/ To have bitten off
the matter with a smile/ To have squeezed the universe into a ball/ To roll
it toward some overwhelming question")

As he's reaching the end of his tedious argument (tedious to him more than
to the receiving end of the argument), the concern of how that question will
be answered stops him short of it, only to resign himself to grow old, to
being a second-string player who never has to ask such a question.

(And - as to grammar - if you want to read it as streets, the phrasing
should be "streets, which follow like a tedious argument of insiduous
intent, to lead you to an overwhelming question...")

Sorry for the rambling...

The beauty of modern poetry - read it any which way you like...