Is there a way to query for a file upload, and for text entry, before one gets to the checkout set of screens?

And more specifically, I have not quite figured out how to query for a file upload (of an image) tho that appears to be a function of assigning attributes.

Do a file upload attribute and text entry attribute.

You really need to get the zen cart book...

Basically what you will do is enter the product (in your case the picture?). Add option names (text and file upload). Then assign those attributes to the product.