Can pytesseract use ChoiceIterator to search over multiple matches? It seems to me that pytesseract is only an interface to the binary. tesserocr gives access to the Tesseract API which allows the use of ChoiceIterator. Example How do I use the Tesseract API to iterate over words?
pytesseract
"wraps" tesseract executable, which does not provide this feature. So you need to use tesserocr
or you can use tesseract API via cffi.
You did not specify why you need ChoiceIterator. Maybe have a look at hocr output (which is supported by pytesseract.