I drive a 4.0 2001 wj. And ill sometimes put it in 2nd gear to get up a big hill on the way home. Since its an automatic, am I killing the tranny?

What's wrong with putting it in drive?

You have to go from 15 to 35 miles on the hill and it has a hard time shifting. It's a very steep hill.

Well there is nothing wrong with it as long as your rpm's arnt going real high