Re: Forget the geeky stuff, sort out the user experience.
In my eyes, the Gimp UI is not a problem. I am still loosing the toolboxes every now and then, but otherwise the menu's do what they say that they do, inclunding the opening of new toolboxes.
Gimp covers all my personal and professional needs for bitmap processing (including website work).
Expanding my free toolbox, Inkscape covers all vector graphics needs, including backporting pdf's to dxf for import into CAD (reverse engineering parts that do not come with a 3d model).
Libre Office writer is good enough to handle large technical documents including operating manuals with very complex page numbering (LO-Calc remains lacklustre).
If you want a horrible UI, then go look at Blender3d. All other programs (except, maybe dwarf fortress) pale in comparison. This is a pity, since the program itself is getting mighty powerfull. (I work in CAD on a daily basis and I used to handle 3dsMAX in various versions, so it is not a matter of not knowing 3d),