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I don't think there is any "should" about it. Crosscut pipes, most often with the bird's-eye end grain on the sides of the bowl and stripes of straight grain along the front and back, have devoted fans. As do straightgrain pipes, with stripes of grain going up and down around the bowl and bird's eye on the rim and bottom. I own and admire both. But most of my pipes are somewhere in between, with asymmetric patterns on each side of the bowl or with angled grain or less than organized flame grain here and there.
I've not found any measurable difference in smoking qualities no matter the grain orientation (although I reckon some hereabouts will have opinions about that), so the easy answer to your question is: Figure out a pleasing or creative plan for your particular piece of briar and then have at it. You'll likely change your plan a few times as the wood surprises you, but that's part of the fun. It's what makes pipe carving as much an art as a craft.
Don't forget to show us what you come up with!
Billy
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Never attribute to malice that which is adequately explained by incompetence.
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