Update:
Alright figured I'd I do the internet justice and will post an update. I'll get pictures up later today.
After being a bum for about a month and a half, my buddy and I finally decided to do the dirty work ourselves and dropped my Transmission along with the Transfer case. It seems that credit for being closest to the problem may have been
XCM.
Having dropped both the transmission, we "Turn Tested" (Idk, just what my friend called it.) the transfer case. Put the tranny in park, the t-case wouldn't spin, put the Tranny in gear and the T-case would spin. Which apparently pointed to something in my transmission being the problem. The Transmission pretty damn close to brand new looking ATF, and only a very fine layer of metal on the two magnets. No chucks or anything. The T-case looked quite a bit darker and definetly had more metal then the Transmission. However no chucks came out. My companies mechanic recommend for me to take the Torque converter off next, which also seemed fine upon inspection.
I figured before I dig any deeper it would be best to do my due diligence and take apart the t-case since apparently those are much easier then Transmissions.
However, after the bribery of our company mechanic with the promise of beverages of his choosing he said he'd do it for me.
Inside we found several... problems. And what according to him what was almost definitely the problem. It also could of been the cause of some other noise I had experienced. While off-roading in the past.
1- The Shift fork was worn down to about
half of its width where it would come in contact with the Range sleeve.
2- The teeth of the Range Sleeve were ground down on one side. As it was apparently slipping backwards since the Shift fork was worn down so much. He thinks that it eventually heated up and at speed when the tranny shifted that the sleeve disconnected. But when it was disconnected and no pressure of driving it was able to be hand twisted. Hence the "Turn Test" working earlier. (Or that's what I got out of what he said, haha.)
3- Some Seal looked obliterated. Probably the last piece to give out when it died. (I'll update this later when I get a list of things that need to be fixed in it back.)
4- The Filter/magnet had done their job a little too well and had quite a bit of small chucks all over both.
5- The chain had stretch quite a bit. It was loose almost to the point of rubbing the T-case housing. (Probably a non-issue related problem.)
I'll take some pictures this afternoon, I'm probably going to paint the tranny and replace its filter since we went through the trouble of dropping them both. Currently weighing the option between a Remanufactured T-case from SmartParts Auto or getting an Atlas.
TL;DR - My T-case is definitely bad. Now the PC tech in me says that doesn't rule out the Transmission also having problems. But everyone reassures me both going out at the same time is super rare. So I'm just going to go ahead and replace the problem. Pictures -Pending-