I can not print one photo or pdf file multiple times on 1 page.

In Windows Photo Viewer (your first screenshot), after you select the output format (in your example, 9 wallet size pictures), change the "Number of pictures" at the lower left to 9. Then click the Print button.

Printing multiple images from a PDF is more difficult, at least with Adobe Acrobat Reader. As far as I have been able to determine, you can print multiple images from a PDF file -- as long as the file has more than one page in it.

Assuming you have a pdf file with more than one page, do the following:

First, click the "Size" button and select "Shrink oversized pages"

Now select the "Multiple" button and then select "Pages per sheet." In the example below, I selected 4, but there are various options.

As shown in the preview, at this point, Acrobat Reader will print pages 1, 2, 3, and 4 on one sheet of paper.

If you want to print 4 copies of the same thing, for example, 4 copies of the image on page 1 of this document, select the radio button for "Pages" under "Pages to Print" and enter 1, 1, 1, 1 in the box

The problem for single-page pdf files, such as the following example, is that the options for "Current" and "Pages" under "Pages to Print" are not available for single-page documents. Thus, although the image size is reduced such that 4 copies would fit on the page, only one page -- i.e., one image -- will print, because that is the only thing selected for printing.

Perhaps someone in the Acrobat Reader forum may know a way around this problem:
https://community.adobe.com/t5/acrobat-reader/ct-p/ct-acrobat-reader?page=1&sort=latest_replies&filter=all&lang=all&tabid=discussions