Make insert module add uploaded images to media library automatically I'm trying to get adding images to work smoothly (more like how wordpress handles it)
I have added WYSIWYG+CKeditor, Insert, Media, Resize Filter (which I can't yet get working). 

Right now the main issue is I can insert things from the media library that are already there. But when I'm at the bottom of a post adding an image, I want all added images to go to the media library (especially to make cleaning up unused/replaced images easier for the content editor).

Is there a simple way to set up this behaviour?
Instead of using the Insert module, use the Media module's WYSIWYG integration. This adds a button to the WYSIWYG toolbar which allows you to choose an item from the Media library. You can also upload a new media item which adds it to the library and selects it to be inserted into the WYSIWYG editor. The link above explains how to set it up. Make sure you follow all the steps. You have to enabled this functionality in both the WYSIWYG profile and the text format to get it working properly.

Also, check out this great video on Media for some more information.