I’m in the keep it camp! A newer rig will have more power and comfort, but you can’t replace the character! I had a ‘91 and kick myself for getting rid of it. It was slow and a little squeaky, but it was awesome.
I have a scary hi-lift story that was completely user error. When I was 17 (first problem), I had a full sized blazer with 35s. Got a flat one day and, of course, I had my hi-lift because all of the cool kids carried them. Didn't want to bend a bumper or scratch anything so I stuck the jack into...