A common problem I've found with WYSIWYG or images is often that uploading is easy, but getting the right user groups to see them (e.g. anonymous) can be frustrating...
First make sure the following is unchecked (unless you need it)
Admin -> Modules
CCK checkbox for: Content Permissions 6.x-2.8 Set field-level permissions for CCK fields. Depends on: Content (enabled)
Uncheck - save configuration
Admin -> Content Management -> Post Settings -> Rebuild Permissions
admin/user/permissions ensure the checkbox = upload module -> view uploaded files
admin/settings/imce (settings = site config -> imce) profile name = user 1 Role Profile assignments = anonymous user should have "user 1"... (e.g. can see IMCE stuff)
basically those three things, plus a lot of clear all cache rebuild permissions clear cookies on browser?