I think a winch is a fairly necessary first mod especially if you'll be going out alone. Besides that, do what you said, go on trips and figure out what you need based on those trips.
Love how most of the advice not to regear is from gasser owners. Don't make your decision based on these answers. The decision on whether or not to regear will all depend on how you use your Jeep. This diesel specifically has cooling issues and does not like high EGTs (exhaust gas temperatures)...
Some 15 years ago I took my dad's 05 VW Touareg out to some easy trails in our area. Mostly dirt roads with a couple puddles and climbs along the way. It was the car that sparked my interest in offroading and eventually led me to buying my first Jeep. My dad has kept it over the years, mostly as...
I would advise against ordering your own gears. I bought my own parts with the plan of doing the regear myself. Plans changed however, and most places I called refused to use customer supplied parts. Dana Spicer gears are great though, that's what I bought.
I drove across the entire US like this lol. Clear codes, drive for 1-6 hours, limp mode, repeat. It takes a while for the system to catch the fault again.