Hi Loccom,
If I'm understanding what you're asking, you can't change the "info" fields in an upload field from a text field to a text box.
The way I approach descriptions is to create a separate text box field and use that for description of the upload.
Then I echo the description field in my viewer to insert the description on the web page.
When you're creating a new field you can choose the type of field from the Field Types pulldown list. You can also change a field from a text field to a text box by clicking on "Modify" next to the field you want to change in the field list of your editor. You won't lose any data but you might change how the formatting appears.
There are lots of basic design tips and many advanced recipes, including some on automatically wrapping descriptive text around images, in in my CMSB Cookbook at http://www.thecmsbcookbook.com
Hope that helps,
Jerry Kornbluth
The first CMS Builder reference book is now available on-line!
Take advantage of a free 3 month trial subscription, only for CMSB users, at: http://www.thecmsbcookbook.com/trial.php