Yep, I did use inline images in my days with org-mode, but I found it to be rather hacky. It's possible, I just found it unpleasant.

May I suggest contacting the emacs org-mode maintainers and chat. The emacs guys are very receptive I know, I imagine the org-mode guys will be just as good.

Resizing image is a pain, and inserting quick screenshots takes some hacking around.