Oh man... this is like the sorest point ever for us.
TBH we absolutely know how shitty the experience of posting stuff is. Its one of those things that caused us to completely overhaul the media system, and change a lot of the back-end of the way the site works.
So mark my words, this fix is coming on the chopping block soon. Don't hold your breath, because it might be like a winter/spring sort of deal. We want to fix this and fix it right.
We are newschoolers. Expect us.