Comic Site: What Would Be Necessary?

Lately, I've been working on converting another site to Drupal - this time, however, it's one
that hosts a few comics.

Thank you in advance for any help you can provide, as it will be greatly appreciated.

Overview

A flat-file CMS is used for the comics, with all other pages as static HTML files. Though
the site also includes an image gallery and forums, they will be left as-is, maintained
separately from Drupal.

Currently, each user maintains one or more comics, with each comic using its own copy of
that CMS. The users can also maintain their static pages (and files), but - due to how things
are set up - only the website administrator can upload them.

What I want to accomplish is using just one CMS installation (Drupal) to handle all of this
work - each user could maintain their comics, pages and files without requiring assistance from
the website administrator.

Sections

Each comic has the following sections:

Archive

This is a single page, displaying a list of every strip for that particular comic. They are
categorized by year, with a list item for each strip; each list item contains the strip's
number, date, title and a link to that strip. No sidebar is present on this page.

Strip

This displays the strip the user wants to visit - it defaults to the most recent
strip if one isn't specified. Below the strip is a set of navigation buttons - they
lead to the first, previous, next and last strips, respectively. They are shown for all
strips, though they may not have a link (only showing the image) in certain cases - the
first strip won't have a first or previous link and the most recent strip won't have a next
or last link. Below that is a "News" section, with any news to be reported for that strip -
for one comic, the website administrator and user share this field. Only the comic's front
page (displaying the most recent strip) will have a sidebar; all other strips (including the
most recent one, if not viewing the comic's front page) will not have a sidebar.

Each strip will contain the following information:

Date

The strip's upload date, which will also determine the strip's number. It can be set
to a custom date by the user (for uploading older strips in the proper order), but will use
the current date if one is not supplied. Different pages will display this date in
different formats.

Image

The strip's image. For compatibility with the previous CMS, it will have to be able to
use images already uploaded to the site, along with renaming new images to the strip's
upload date (in the "YYYYMMDD" date format).

Number

The strip's number, based on the upload date of the strip. If any strip (other than the
most recent) is added/deleted, this number will be recalculated for all affected strips,
to account for the change.

Title

The strip's title. Certain symbols (such as the apostrophe and quotation marks) will
have to be converted to their respective HTML entities - this will allow the page to remain
valid (according to the W3C Markup Validator).

Checklist

Required

• Determine what will be necessary (content types, modules, custom code, etc.) to
  accomplish what has been described in this post.
• Set up a theme for each user, which will be applied to all of the comics and pages they
  maintain; the main site itself will also have its own theme.
• Set up the pages so that some will have sidebars and others will not; the sidebars will also
  differ between each user's set of comics, as well as for certain pages.

Preferred

• For one user's comic, automatically update the link to the most recent bonus comic on
  their main comic's page. Currently, one user maintains multiple bonus comics, and
  updating the most recent bonus comic is done with a script separate from the CMS. I am
  looking for a way to add a field to take care of this, so that this script will no longer be
  needed. This field is shared between every bonus comic maintained by that user and
  determines which bonus comic was updated most recently. It is only updated when a new strip
  is posted for a bonus comic, which in turn will update the most recent bonus comic's link on
  their main comic's page. Optionally, there will be a file upload field to upload a graphic
  displaying part of the most recent bonus comic, if one hasn't already been uploaded.
• Allow each user access to upload files to their respective folders under "files" and
  "themes". This way, the website administrator won't have to upload files every time
  something changes on a page.
• Allow for more than one user to post to the "News" section of the comic, so each user
  can update their own news independently instead of sharing a section.
• Remove the "News" section entirely for certain comics, as no news will be posted in them.

Optional

• Allow each user access to rename and/or delete files in their respective folders under
  "files" and "themes".
• Place the "files" and "themes" folders outside of Drupal's directory, for easier
  maintenance.