2 years ago, I turned my 98 XLT 4x4 4.0 SOHC into an offroad only truck. Ive done a lot of mudding, trail riding in those two years, and have a couple of suggestions.
1) T-case - You said re-gear it. I'm not sure you can regear beyond the 2.68 (4lo) planets that are in it now. If you can, i'd be interested to know that.
2) Rear locker or minispool. Since my X is offroad only, I put a mini spool in the rear. Its fine in grass/mud/dirt etc. And it never sees the street. I dont have any issues turning, either. I thought about an auto locker for the rear, but I took the extra $200 and bought an auto locker for the D35 front instead.
3) Gears - If I read it right, you are looking at 3.55s. My personal opinion is to go much lower than that (numerically higher). Mine has 3.55s and 33x12.50 tires, and while it still has some pep, it's a pig on the trail. The OHVs didnt make as much power as the SOHCs either, so I would go 4.10 at a minimum. But if I were you I would go to at least 4.56s. I just bought a set of 4.88s to drop in after the first of the year, because I want to go to 35 or 36s when I need new tires. Also, with the 3.55s and 33's offroad it tries to constantly shift. I think with the 4.88s I wont need to always be in 4lo, and can let the trans better decide when to shift.
4) Lift - You know you are going to want larger than stock tires, so figure out how you want to lift it. I've got a 1.5-2" suspension lift (TT and WAR153s), and a 3" body lift, and I dont rub 33's at all. Had a lot of people look at me funny about the body lift, but I did it primarily to get the running boards above the frame rails. Now if I roll over a hill, fallen log, etc, the frame rubs, not the running boards.
5) Snorkel - Where there is mud, there is water. Lots of people have different experiences, but with the stock air box and the silencer pointed right at the front, my X took a big drink of water from the creek we were crossing. Fortunately it didnt hydrolock, but I learned my lesson and put a snorkel, new vent tubes, etc.
6) Skid plate - Actually plates. If you can find or fab a front skid plate, and one for the t-case area, you'll be glad. Before I got mine I broke a Trans cooling line, and yanked the plug off the t-case shift motor. It doesnt take much of a stick to do some damage to your lines and wiring underneath.
Good luck on your project. I think X's are way underrated when it comes to their capability off-road. I've been impressed many times.