I was thinking about this recently.
The requirements for getting a pipe burning aren't much different from a campfire.
As far as packing goes, if you spread a bunch of sticks across the ground, you're not going to make a very good campfire. If you just take a log and plop it in in the fire pit, you aren't going to have any success either. One doesn't have enough density, the other has too much.
If you want a decent fire to start burning quick, it needs to be mostly small pieces, mostly in one place. Fire needs to be able to spread from one piece of wood to the other, and have air flow between them.
The requirements for packing aren't terribly strict, tobacco needs to be tight enough to spread embers but loose enough to allow air movement, which I'm pretty sure is a fairly broad range.
But, stacking wet logs together still doesn't get you a campfire.
As an example of how far this can swing in the other direction, sawdust in the right particle size and air mixture can be explosive, and chances are the same could be accomplished with tobacco. Not that we want to create an explosive pipe smoking experience, but the point remains, the more surface area your tobacco has, the better it will burn. The more leaf fibers are exposed to the air, the more fibers will burn when you set fire to your pipe. Rubbing out your tobacco is an important step.
Some of the most experienced Pipesmokers on this forum use of a small blender to do the "rubbing out" for them. I haven't tried it just yet but it sounds like a great time saver. just make sure it's an implement you can dedicate to that purpose, tobacco is probably not a flavour most people would appreciate in their milkshake.
If you swing all the way back to the wrong end of the spectrum and try starting a campfire with wet logs, but this time with no restrictions on your starting methods, "More Power" is still sort of an option. If all you have is a pile of logs, they can be made to burn, a large Propane torch will work wonders. Not for your pipe, don't use Propane on your pipe, but I can stuff a flake in my pipe and make it go using a Butane torch if I want to. It smokes just fine as far as I can tell, but it does take a little longer to get going, and using a Butane torch runs the risk of scorching the rim of my pipe. So on some pipes a Butane torch might be everything you need, other pipes not so much (it also depends on what company you keep, burnt rims being equated to "wanton violence" by some).
Unfortunately moisture is a subject all on it's own. Sometimes you want more and sometimes less, but it's probably best to concentrate on getting a bowl burning properly before worrying about getting the most flavour.
For what it's worth, five or six re-lights sounds pretty good. I wouldn't worry too much.
and welcome to the forums.
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