First resize you JPGs to 8" wide and 72 dpi for faster loads and a forum sized image.
Select the text in your Word doc, Copy it, and then Paste (Control V on a PC) in the Commentary box.
Place your cursor where you want to insert an image - usually a new line - and click on the InsertImage button to the upper right of the Commentary box. You will then have to browse for your JPGs, name them, and upload.
After you post you may have to edit to get the spacing right.