You can try to force images onto the same page as the caption by putting them in a paragraph together. But you can create a problem with it bleeding over onto the next page that way, because the whole thing is too big for a page.
If they must stay together, use your graphics program and put them on the picture. But this lacks flexibility, is a lot of work and may not be appropriate for some pictures. However, it does have a sort of old-time appeal. They used to write the date and so on right on the picture in a number of older ones I have seen.
Since it seems primarily for your family's use, whatever you choose should govern.
You might want to consider how you would add pictures which are offered to you of members in earlier stages of your book once members of your family have seen it and how you would add pictures of the next generation and beyond, if this is to be an ongoing thing.
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