I'm just a newb too, but here are my impressions:
1. Some people are "clenchers" and some just aren't. I am experimenting with it, but being so new to pipe smoking myself, I find myself wanting some light so I can see what I am doing and lots of looking down the bowl. I think when you are totally acquainted with a certain pipe with a certain tobacco, it becomes second nature and requires less looking and tentative fiddling. That being said, a lot of veteran pipers on here are just not clenchers.
2. There was some discussion somewhere recently about a pipe meant to smoke upside down. I don't think you will have good results with a conventional pipe, but as everyone loves to say YMMV (Your Mileage May Vary). I think that is a good reason to get out of the rain, get a really classy umbrella or a really really big hat.
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Rookie, but learning.