Online ad order system?

The publisher of the newspaper where I am building a new site in Drupal/ProsePoint wants to move the "Lifestyles" announcements (birthdays, birth announcements, engagements, weddings, anniversaries) into an ad section (in the print version of the newspaper) called "Celebrations."

And she wants people to be able to place orders for "Celebrations" ads online.

Which means that people need to be able to fill out a form online with the requested information (for example, for a birthday ad, it would include the first and last name of the person celebrating a birthday, the gender and birthdate of the person, details about the plans for a party or celebration, etc.) and then be directed to a "checkout" where they can pay for the ad; then an email would be sent to us, letting us know the size and type of the ad (each of the five categories above will have four sizes; each size will have a different cost; within each size will be the choice of horizontal or vertical) and giving us the content of the form so our composing department can create the ad.

I've been looking for a way to create this in Drupal; I thought that Ubercart + Webform (using Webform Associate and Ubercart Webform Productize) would be the way to go ... but here's the problem:

Each of the ad sizes (all 40 of them) would need to be set up as individual products in Ubercart. That's not the hard part; the hard part is that the associated Webform has to be created DURING the process of setting up each ad size.

Which means that I have to create 40(!!!) webforms. (And some of the larger forms may have 20-50 fields.)

I can't create one Webform for birthday ads, for example, and then clone and revise the form for each ad size (the form will have more fields for larger ad sizes and fewer fields for smaller ad sizes) and then somehow link the form to the appropriate ad size.

Any ideas or suggestions?

Sincerely,
Katrina