* Files & Images
* Users and Roles
* External services, either relying or providing
Could be delivered in html/xml format or as a database dump.
Need to determine how to organize content so that the drupal cck content types, taxonomies or other can be created.
Is there a commenting system and are the comments to be migrated.
Files & Images
How are files stored, can the path be referenced directly, or do they need to be stored as nodes. For images, use the image module or imagefield?
Users and Roles
What users if any to migrate over, how does the access system in the old site translate into drupal's user access system?
Does the site provide feeds or other services? Or does the site depend on other external services such as Amazon, Youtube, etc. How will the interaction be translated?