I can imagine it said, semi jokingly, with careful stress and pausing.
In writing? well, I had to read it four times before I understood it. I was a more than a little confused reader.
Interestingly, as soon as I had written that last sentence, it seemed less unlikely to me than yours. Perhaps it was the underlined words that confused me: He is an a little poor boy.
Or perhaps it's because I may be a little confused, but I don't think I am likely to be a little poor.
Or (will this never end?) it's because the idea of a poor little boy came to mind and muddied the waters.
Student or Learner