TIG, that sounds like a the type of solution I would be looking for, although I was hoping there was an existing plugin that does something similar It does seem like good practice for some scripting though, so I will definitely give it a shot in the coming 2-3 weeks (I am pretty basic at scripting as well, so it will take me quite a bit of time)!
Pilou, I am not sure I understand. My problem would be that I would not only have to apply each of the 200 different textures (not repeated as in my example screenshots), but also adjust them to fit perfectly within the hexagons. Could ThruPaint help with that as well? From what I gather from the descriptions I read, it doesnt really have functionality for this purpose?