"used to" with the past perfect

[Phaedrus]

I was wondering if my fellow native speakers find it acceptable for the past perfect to be used with used to:

(1a) I used to smoke.
(1b) ? In 1995, I had not used to smoke. (versus: In 1995, I did not use(d) to smoke. / In 1995, it was not the case that I used to smoke.)

(2a) He said, "I used to smoke."
(2b) ? He said that he had used to smoke. (versus without "backshift": He said that he used to smoke.)

The (b) sentences do not sit well with me, but I can't quite say I find them ungrammatical. What do you think?

Thank you.

[GoesStation]

They worked for Jane Austen. They don't work for me.

[Phaedrus]

What about this? Does this work for my fellow natives? It seems to sit much better with me, but I have mixed feelings.

(3) He may/might have used to smoke. [to be interpreted as meaning: "It is possible that he used to smoke."]

It's a different use of the perfect. It might be called the "modal perfect," as opposed to the present or the past perfect.

I realize this changes the topic slightly, but it is still close enough, I feel, for there to be no need for a separate thread.

[GoesStation]

What about this? Does this work for my fellow natives? It seems to sit much better with me, but I have mixed feelings.

(3) He may/might have used to smoke. [to be interpreted as meaning: "It is possible that he used to smoke."]

I can't imagine saying that. It wouldn't occur to me. He might have smoked once is a natural way to express the idea.

[Phaedrus]

I can't imagine saying that. It wouldn't occur to me. He might have smoked once is a natural way to express the idea.

Or:

He might have once been a smoker.
He may have smoked for a time.

With used to, the meaning is not just a past occurrence (He smoked once) but a past habit (He smoked regularly).

[GoesStation]

Or:

He might have once been a smoker.
He may have smoked for a time.

With used to, the meaning is not just a past occurrence (He smoked once) but a past habit (He smoked regularly).

I should have said He might once have been a smoker. That's unambiguous.