You could do that, and create seperate popup templates for each field… it would work…
Personally, I’d go with Gallery Extended module. It allows you to upload photos and “relate” them to weblog entries. With a special loop, you could display all related photos alongside the weblog entry.
It has an SAEF form, so it could be done via the Front end. One thing to note is that if you’re doing this through the SAEF, it would have to be a seperate template for the uploading. Basically, you would need to have the weblog SAEF form on one template, and with the help of Solspace’s SAEF Redirect, you can control the redirect to point to another template - with the Entry ID in the URL. This would allow you to dynamically set the Gallery Extended SAEF Form template to know which weblog entry to relate the photos to.
Alternatively, Gallery Extended now has a built in “Image Tab” in the Publish/Edit page in the CP, so you can easily do this there as well.