here is my worthless 2 bits.
Take the plunge and do the 8lug swap and sterling. if you are starting to hammer on the truck more, and then add 37's, you are going to start hurting that 8.8. The shafts seem to be plenty strong, and in fact I think their diameter is like 1.3 or so, so they are fairly strong, but the tubes are seeming to be the weak point. I know dave blew his up at the tubes and spring perch, and mine are in the process of failing there. thus the sterling, aand then thus the 60. ( i couldnt see a reason to have a one ton rear and not a front. evil bronco always wanting more money)
the 44 with warn$ and ctm$ will be strong for the most part. i dont think you will have any probs, or few, with the shafts/uj's. the knuckles will start to be the weakest point. You will want to start carrying a spare set, and prolly spindles too. When I was going to stay with a 44, I was looking to have a complete spindle out, (with balljoints, bearings etc) ready to go in the spare parts box while wheeling. I also have/had a complete set of spare shafts assembled with uj's ready. With all my buddies here running 44's, we got really good at swapping joints and stubs on the trail, so I figured I would save the time and just swap everything, thinking it is faster to tear down and put back together, then add fixing time in there too.
Ball joints, knuckles and hubs are going to be your weakest point, so just expect to fix it and you will be fine. this was not something I wanted to deal with frequently, so I bit the bullet and went 60/10.25.
As for the 9", I am sure I dont need to tell you this Dustin, but forget about it. it would be a waste of time to do that and not the 10.25. Also, forget the mosers for the 8.8 and what ever build ups you can do, just go 10.25 if you are going to do that. you are where I was a few months ago. I knew I wanted 37's ( at least,may go as big as 40's with my 5.13's), and I just started talking with people and looking at everything/all the variables. wih that tire size chioce, you are pushing your limits, and at the low end of 1 ton stuff. you can get a 10.25 pretty cheap ( i got mine on half off day at PnP for 75 bucks) the locker was like 550 on a deal, and then gears, which you are going to have to buy anyways. You could always just get the gears and weld it:shrug if you can deal with the road habits.
As for gearing, I would say at least 4.56, better to go 4.88. i am going 5.,13 cause i am tired of taxing my tc all the time. I am sure you know with the e40d, 4.10s and wheeling would kill your tranny with 37's. Way too much heat.
sorry for being long winded. Like I said, I had the same "come to jesus" debate a while back. good luck, will be interested to see what route you go.