With Joomla one third party has taken the TinyMCE image manager to new levels:
http://www.joomlacontenteditor.net/His extended image manager presents you with a very neat file browser and all the image possibilities all wrapped into one. You can upload image (with a redesign of plupload), resizing the image AND creating a thumbnail as you do so which is automatically placed into a thumbnail subdirectory that it creates on the fly. You can then select a full size image that you want to display in a shadowbox popup and it will fill in the details of the thumbnail to be inserted into your article for you. It also can crop and resize any existing image and so on.
He really should be brought on board (might need a bribe as he is a one man band and this is part of his business). His extension already has a comprehensive joomla management system so you can define exactly what roles (groups in joomla) can use what bits of the editor - easy to define different plugins, editor buttons, layouts and so on for each role. He also has plugins for media management, non-image file management, full screen options, template management (not needed with Liferay) and so on.
His business model means the core version is free but he charges for the more clever extensions, though not much.
Meanwhile, here is your shoehorn - It is an absolutely mandatory piece of equipement for anyone attempting to fit a software solution to a clients real needs when you cant be bothered to do it the proper way!
(I apologise for too much idiomatic English)
Joss
