Once I had an image workflow I loved!

I am a convert from Wordpress and am struggling to get a grasp of how to handle images here on Drupal. I'd love to participate in the discussion. At one point, before an major upgrade, I had a great recipe for images on the Wordpress side of things. I'd like to share this and see if I'm missing some modules or tricks that I haven't found yet, or if some of my desires don't mesh with the Drupal way and have some future pitfalls lurking.

My recipe was as so:
1. At content creation images can be uploaded, browsed and manipulated. (Accomplished with IMCE. Love it!)
2. Thumbs were created at upload automatically or via checkbox. (IMCE)
3. Original and/or larger Images were uploaded to S3. (????)
4. Thumbs could be included in content via popup type form with pulldown css classes. (BUEditor. Love it also!!)
5. Pop-up form has option to link to larger sizes and use lightbox. (I've accomplished 4&5 with with two separate buttons in BUEditor, but would like to merge the two. I just don't have the skills! )
6. Large display images shown via lightbox could be included in an in-line in-content gallery (Oh how I wish Drupal had this!) with automatic cropping and cssiness.

Attached are my two buttons that I hope I can merged into a single button one day!

Change "bueditor_buttons.csv.txt" to "bueditor_buttons.csv". CSV files are not allowed.