Let me have a go...
1. Me, I prefer to see raw, natural wood in a new pipe, not the pre- carbon coated variety. That's regarding a new pipe. On a well smoked pipe it is possible someone would ream out the chamber thoroughly, removing previous carbon build-up. In either case you'd be talking about a non-carbonized bowl. A thin coating of carbonization protects the wood in a pipe from burning.
Thank you for explaining that...So, would you recommend a Non-Carbonized pipe to a newb? I have a few, so I have smoked already, but the last thing I want to do is crack a pipe
2. Tobacco moisture meter for ribbon or shag cut. Squish a wad between your thumb and index finger; it it squishes and -
i. stays squished, it's too moist and needs a little drying out
ii. springs back, it's probably good to go
iii. crumbles to dust, it's way too dry and needs remoisturizing
Perfect, so I think my tobacco is in the right mixture then 
For flake tobacco, if you bend a flake 180* and -
i. it bends like rubber and nothing breaks it's very moist
ii. it bends but fractures a fair bit at the bend it's about right (for me)
iii. it snaps in half it's probably dried out and might benefit from remoisturizing.
3. You're packing a bowl?! It's too tight. Never pack, fill. Too loose a fill and you can always moosh it down a bit after lighting. Too tight from the get go - ferget about it. You'll suck your cheeks off trying to keep the pipe alive. I routinely produce large, almost opaque clouds of smoke with small-to-modest sips. Getting there is finding the right balance between pipe, tobacco and filling technique. When something isn't working, make a change. It's like sex - timing and technique.
Ok, maybe "packing" was the wrong word to use; however, now...maybe I was lying, and maybe I am packing it too tightly...after all, the pipe is running a little hotter than I would like it to while puffing. Perhaps that is from things being too tight and me having to frequently puff to keep it lit. I'll work work on my technique...geez...same answer i give my wife! kidding!
Here is a recent sip-cloud:
Too wet, you think? That's easy to determine. Is the pipe drooling into your mouth instead of the other way around? Is the heel of the pipe wet and swampy? If so, the pipe and/or the tobacco are too wet to smoke. Consider dry time for pipe (24 hours) or tobacco (let a wad sit out 30-60 minutes).
Yea, no worries here then, thanks!
4. I never could equate pipe tobacco with cigars. People talk about it a lot but, for me, it's like comparing pumpkin pie with whipped cream to aluminum billets. They both have their purposes but have nothing in common (for me). I like cigars and pipes but I sense them in totally different ways.
Guess once I figure all this out really good, I'll just have to follow the one main rule...Smoke what you like, like what you smoke 