Custom Poetry PDF Website – Strategy?

I’ve been tasked in creating a website which allows users to look through some poetry, check off which poems they want, and then hit submit and be brought to a generated PDF of only the poetry they’ve selected. In addition, the users should be able to upload a few photos that can also be included in this PDF. This project is a little above my level, but I think I can handle it, and I’ve come up with a strategy for how I’d like it to work. It would be really great if I could get some feedback from more experienced web developers on whether or not I’m going about this the right way.

My user is going to be the only administrative user in the WordPress installation, everyone else who accesses the site will be asked to log in. Each poem will be a post, so that I can divide them into categories. I’ll code some kind of check box at the bottom of each post – when you click it, the post # is recorded into a custom MySQL database. Every user will be given their own row in the database, where the first column contains their username and the rest contain the posts they’ve checked off.

I don’t really know how I’m going to do photo uploading…any ideas? I don’t want to give users access to WordPress’s back-end photo uploader if possible.

Finally, when they’re done they can go to the Submit page, where clicking the submit button executes a custom .php script. This script will run through their user’s section of the database, adding the text from each poem they’ve checked off into a custom file named TheirUsername.html. At the end of the script it will activate a free HTML to PDF script I’ve found online, and thus convert the .html into TheirUsername.pdf, and provide the user with the link.

This all works out in my head…but as I said before it’s more complicated than any of my previous web jobs, I’m pretty new to this. Does anyone have any suggestions on how to get this to work (better, or at all?) Thanks so much.