Image Upload with mass importing of listings

I loaded my first file of 700+ business listings…but there are thousands more to add. I’m trying to perfect the process before I add more.

I started with your sample import file but how can I modify the upload file to include an image (as the Company Logo) with an “Enhance Your Listing” image. See the two attachments to help further explain what I trying to accomplish.

I did try to use Column X in the sample import file (post_images) with a .jpeg file but where do I load the picture into the directory files?

Furthermore, have a link attached that opens a new window to the Package which business owners can enhance their listing (www.biddydiddy.com/add-listing).

My thought is, once a business owner Enhances their listing, they can upload a new company logo that will override the “EnhanceYourListing” picture.

Thanks in advance,
Al