Thanks guys for all your help thus far. I'm waiting for a buddy to help me out, but a quick update I forgot to mention earlier.
When I put the transfer case in 4H, sometimes I have to release the clutch pedal a little bit and I can feel it go in. One time I heard the gears clunk in and I had to roll it a little bit to get it. That being said (and the fact my 4WD light comes on) tells me that I am going far enough back with the shifter and engaging the high gears.
Also, when I put it in 4H and crawl under... The plate that holds the rails is unseated from its slide, and both rails are still connected. The boot and everything else is off. I will drop the skid plate again later today to try and get a better look at it.
Again guys, thanks for all of the help/ideas. It's in the 70's here all week and I wanna get it out of the garage!