[Mister Moo]

Great start! Great questions! Welcome.

Save yourself some aggravation about break-in and cake and reaming and all that jazz and get you a couple of full-sized Missouri Meerschaum corncob pipes and a pouch of Carter Hall or Prince Albert pipe tobacco - American classic combinations. Learn how to fill the pipe and light it evenly with anything except a torch - puff until it feels hot then stop puffing until it cools down. Do a little snorking. Get a grip on that and then start thinking about that briar. Or smoke cobs forevermore... many do because they are excellent smoking pipes and cheap/easy to learn with.

Something about a pipe that's way different from a stogie. You can smoke half a pipe, put it down for an hour or until the next day, then fire it back up again. Most of the time they taste the same or better - rarely worse.