Tricks? automatic trans..........transfer case shifting.......

67redcudavert said
The owners manual for my wife's 98 Wrangler tells you to put it in neutral and be barely rolling to get it in low range.

Yep, you have to let the gears slow so they can engage but still be turning a little to mesh.
You might also find out that you have a bit of a bindup when trying to get it out of 4x4 and backing up a little helps that a lot.