IF someone has the skills and the time to jump in TS with me some time and school me on this SKINS thing, I would greatly appreciate it!

I have youtubed this to death and i just can't wrap my head around it.

Hit up raptor, he's the Mack daddy

I couldn't tell you anything about GIMP or specifically using that for skins in DCS, but as long as you have something to save or convert images to .dds (specifically DDS DXT5) format you're at least started off. Then you gotta arrange the description.lua to make it actually usable in-game, but that's pretty easy to figure out.