So I realized I forgot to update with some pics of the 8.8 swap.
The swap more or less went well.
8.8 set in a mocked up
And assembled and sitting back on her own feet
I ran into quite a few problems during the swap; the initial hole that was burned into the tube, seized bolts, stripped bolts, one of the Ubolts that RuffStuff sent out had the threads pitched wrong and I couldn't get a nut on it (even after spending over an hour cleaning threads, chasing the threads, cutting it down to try again, etc) and had to buy a parts store ubolt to keep moving.
In the end I got it put together sans the ebrake cables, but somehow didn't notice that with how the new shock mounts are positioned, my shocks are now too long. The ride home felt rough an bumpy and I couldn't figure it out until I started poking around. I finally realized that my shocks only have about 1/2" of up travel now!
I've since ordered a Teraflex shock relocation bar and I'll see if that helps. If it doesn't completely solve the issue, I'll be ordering a set of MORE shock brackets, grinding off the RuffStuff ones, and moving the mounting location to extend the shocks further. As of now the Jeep is on light pavement duty....