Thinking longer term, once you put that supercharger on there, the stick is much more simple, which means less things to break with the stress of offroad.
Also, an automatic doesn't have full lockup in 1st gear (I think), so you can't use the compression of the engine going downhill to slow you down (and to me, downhill is a helluva lot more scary than uphill). Had a friend once with a mid 90s cherokee that wired his automatic to lock up the converter in 1st gear (with a switch, it will stall the engine if you stop).
I have a stick in my Cherokee and it took a long time for me to learn how to use it offroad. In my opinion, it's more work, and takes longer to learn, but if you are serious about offroading it will be worth it.
So what did I do? I got the auto. go figure...
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