Ok I did some more testing...
My little experiment started with verifying that every skin worked prior to starting. All 20 skins worked.
Next I edited 4 different skin inis. I used the following skins: ArcX, Armageddon, Armageddon Widescreen, and AtomGuy. I renamed them As follows ArcX = Armageddon1, and AtomGuy = Armageddon2. The others stayed the same. The Skin inis were also updated to relect the changes.
So.... Now I have 4 test skins with the first 10 characters being the same. Next these 4 skins were added to the skin folder on my xbox. Rebooted and... They all worked.
So this disproved my earlier attempt to figure this damn thing out.
So I then removed the 4 test skins. Since I already had Blackbolt Console and blackbolt_S loaded I decided to test it again with these skins. So I added blackbolt and blackbolt_elite to the mix. Rebooted... and blackbolt loads as the default Evox skin.
So now I'm wondering if its something specific the blackbolt skins I have. Yes I checked the ini file to make sure it was correct. And when I deleted just the blackbolt skin a different skin, named X OSX, loaded up as the default skin. Only minutes before it had worked, prior to deleting the blackbolt skin. (Whenever I changed something I went through all the skins to verify functionality).
In order to fix this I deleted all my skins, rebooted, and added all my favorites minus blackbolt and blackbolt_elite. Every single skin worked.
So I will be focusing in on these four specific skins: blackbolt, Blackbolt Console, blackbolt_elite, and blackbolt_S. I think renaming and adjusting the inis will solve it. If someone else has time, lets get some independent confirmation here. I hope this leads somewhere. Damn wild goose chases.