Towing and Gears

Others will offer better advice, but seems to me if you're going down that road, plus regear, and assuming you're paying someone else to do the install, you may want to broaden your search to consider fully assembled, bolt-on Dana 44 packages. Obviously more expensive, but you seem committed to investing in your Jeep.
I know, I have agonized over that decision. I am all about reliability, which is why all of my mods are done with purpose and done in the best way possible.
One thought I have is to do the regear, do the other mods including getting a trailer, then upgrade to the 44s. This way in the short term I get all the things I really need, then get to the 44s. I know it will be more in the long run, but I can make that work. I read that someone had done some something similar and it worked out because he got good money for his 30/35s.