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Seeking Advice on Site Layout and user uploads

  • My very old FrontPage site has about 1500 web pages of historical photos and text and most all these pages contain a single photo with captions or a long history about the photo. I want to convert this site to WordPress (I think) and need some advice as to whether WordPress can do what I want listed below. I can’t find it in the forums. See my links below to understand what I’m talking about

    Questions
    1. Ability for users to add comments and photos (with permissions) to an existing single web page.

    2. If a plugin is required, which one?

    3. I really need help trying to figure out how to organize this site if moved to WordPress. Photos of buildings are listed by state and city on a single page with links to each. Class photos are listed by class number. Each of these links takes you to a page with the single photo and comments. This creates a lot of extra work. Is there a better way to organize this data so that it’s easy to navigate and search content?

    Home Page
    http://www.atchistory.org/

    Facility photos (there are hundreds of pages linked from here
    http://www.atchistory.org/History/FacilityPhotos/index.htm

    Class Photos
    http://www.atchistory.org/classphotos/PhotoHome.htm

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