How to use Drupal for managing a public website together with an intranet and an MSSQL database? I'm new to Drupal and I've been digging through the documentation to find out most of the features and possibilities of this software.

I'm asking you an advice in evaluating if Drupal could be the case for a CMS for a client of ours.

The client is an Italian public administration; right now they've got two sites: internet and intranet. The two sites feature different layouts and different content (some content is mirrored in both sites, some is only on internet and some is only on intranet). Right now everything is managed manually with classic xHTML and some programming.

In an effort to switch to a CMS (don't consider content migration right now) we have to deal with different infrastructure problems, such as:


the intranet site is behind a private LAN not accessible from outside
the internet site is on a DMZ with no link with the private LAN (and they want to stay it that way)
the client database option is SQL server (they could provide access on a shared database from both sites, this is ok, but it is the only link they could give)


So I have some trouble to find a good software that could solve most of their problems.
How to:


Let them have only one administration panel (content is managed only once)
Let them choose if the content added has to appear on one of the two or on both sites
How to sync the files uploaded on both sites (if files are stored in the db it shouldn't be a problem)
Is there some module that can let editors to insert images directly in articles (let's suppose they have wysisyg editors for content) and save those attachment in the db (same problem as n. 3)
Manage different layouts on sites and also different content organization (menù, views, blocks etc.)


What do you think about it?
Drupal can most of this very well. 

Someone with more experience can address how it can be set up for Intranet and Internet. It can handle multiple sites linked with data from same database (Not sure if this is what you want).

User permissions can be defined effectively down to the smallest content level so restricting access based upon any user categories you choose is not a problem.

Drupal works from a database (MySQL), apache, and php.  Transferring data will not be a problem for an experienced DB manager.

Images are stored as separate files on the site with references in the DB.  Images can be handled in a variety of ways on any page display including direct insertion.

Page layouts can be handled either through layout themes that handle HTML and CSS management and are fully customizable.

Drupal is exceptionally flexible and can do just about anything you can imagine.  There are hundreds of modules to choose from (all free and open source).

Having said all that, doing sophisticated site features is not for beginners and there is a steep learning curve for new site developers.  Getting a sophisticated site up and running requires an experienced Drupal developer.  Some of them are on this site and you can find others at Drupal.org.