Configuring WYSIWYG editors and image handling is a laborious process, riddled with caveats and best practices. The number of contributed modules extending the WYSIWYG experience is vast, and their configuration can be a quagmire.
WHAT WE'LL COVER

We'll go over how to consider input format creation.
We'll look at how (and why) to configure better_formats and wysiwyg_filter.
We'll talk about inline image options and why you might choose one method over another (IMCE vs insert).
We'll cover some helper modules and configurations for image handling (filefield_paths, filefield_sources, pathauto , transliteration, insert, image_resize_filter, imce).
We'll touch briefly on building Features of your configurations, and also pushing configuration into profiles
We'll look at both D6 and D7, but mostly 7.

The presentation will be accompanied by an installation profile and Features to get you from 0-60 in a speedy manner. The assumption, however, is that you're already part of the way with your configuration. The methodology we'll follow is explained step by step in this google doc so you can pick up the parts you need.

Questions answered by this session:
How can I get my administration theme look identical when editing content as my front-end theme on save?
How can I filter out the junk pasted in from Word?
How can I allow a set of users (i.e. marketing dept) to browse and insert image assets into a textarea?
How can I find a happy compromise between security, maintainability, and ease of use?
How can I build Features of my configurations, or push configurations into Profiles?