Crop .pdf Files And Manage With A CMS?

Am asking for input on a better way to manage website content. Input is dozens of .pdf files up to 11 meg in size containing one to eight advertisements comprised of both text and graphics. These files are 300 dpi at CMYK and I use the same .pdf files the printer uses to print glossy paper coupons. The goal is to categorize and display the ads in a website for online printing. This post is all words and no code.

The work flow is divided into cropping and displaying.

For cropping: having done it many ways (screen scraping, Photo Shop. Paint Shop, etc.) am getting the best controlled results by opening each .pdf in GIMP, hand cropping each ad and saving as a .png file. Now using GIMP because the others have been awkward to use or didn't provide the results I want. Have tried various pdf utilities to extract each ad intact and avoid cropping altogether, but the mixture of text and graphics gets skewed.

For displaying: I hand update the html directory and when an ad description is linked by the site visitor, pass filename and title parameters to a common php script I wrote that determines the image dimension based on the image size, builds standard html code and displays the ad. For printing I rely on the browser print button.

Will ASP permit me to develop a web-based application that will read these .pdf files directly from the printer's server, let a non-technical person easily crop them, describe them, store them, build the directory, and display them? Kind of like a cropping content management system? also will need the ability to stick in an impromptu ad here and there too.