Could you guys help me figure out how this would work?

Hey guys, got a question.

So I’m working with some friends of mine who a site that is doing something they call the "Lifestyle Challenge," in which guys are all competing (in a friendly, supportive kind of way) to better their lives through these tasks and challenges (in the form of prompts).

What I want to do:

• Have a user screen in which the prompts are shown: Has button/text saying if you’ve completed it or not, and if not says "Do it!"
• Do it! Screen: Response Page where you could write down your adventures and upload pics as well
• Collective Tracking of your Progress: Basically showing a person or yourself all of the prompts and your responses to them
• Comments page for each person’s "Do it!" response to a promt

I realize the place to start is blogging the prompts with Ditto onto a User Screen...but past there I’m somewhat lost...
I don’t know really how tagging works within ModX, nor have I ever implemented comments...

Here’s multiple ideas I’m still thinking though:
Each person gets a folder. When they click on a prompt it goes to a blogging a page screen. Automatically (and hidden) it will have in the longtitle (or tags?) the name of the challenge prompt. Then on a collective screen showing everybody’s response I could do it by using ditto from a parent folder to all the users, displaying only those with the longtitle/tag the same? Commenting from there would then be easy too, right?

Each prompt becomes a folder and responses are put under it. Collective Screen is just ditto going through that folder and displaying all responses. Comments would be done by turning each response page into a folder? Tracking a person’s history would involve some kind of Ditto search through a main folder looking for a specific username?

I’m not quite sure how to implement either of these, really...Also, would there be any way to make it less freestyle writing? (i.e. Response made up of different sections, like "Did you like it?" "Name three details", etc.) I still (after using modx for a decent while) have almost no understanding of TVs and how they work...

Tricky tricky tricky...

One big question... how many people are going to participate in this? Is it a finite number (e.g. you and 10 friends)? Or were you envisioning this type of functionality for any new web-user who creates a profile? The former solution is of course much simpler and you could theoretically set up user-specific pages with a blog/comments type of display for their challenges/accomplishments.

Doing this dynamically for all users is a lot trickier... I’m at a loss of how to do that cleanly... I’d want to use a Snippet to read information about each user, but then you’d probably need to build some custom database tables to store info about each user... and once you start doing that, you’re into some difficult areas. Hopefully someone else has better ideas... I tend to over-engineer things and make them too complicated.