I am only smoking pipes since the early Spring of '12, but since I am an addict (with everything that I try twice - and like), I have packed what seems like thousands of pipes. I have read, watched and practiced. I have tried the three step method, the Harry method, the Frank method and the Air Pocket method.
I smoke aromatics, exclusively.
For me, the ability to light a pipe "the first time" depends on the pipe and how much attention I am paying to lighting it.
For example, I usually pack a cob when I walk the dog. I don't light it until I am out of the house - walking. I find that I have a serious problem lighting it, often taking five lights to get it going. I haven't figured out why, except all evidence points to the fact that I'm walking since I have few problems lighting cobs in general.
I have a Kaywoodie 95B pot that I can't seem to light right, no matter how much I tinker. I am confident that I will one day figure out how to keep a pot happy, but that day hasn't come.
I find that the Air Pocket method works best for me most of the time; again, this depends on the pipe. I am also not very careful about whether there is an actual air pocket or not. What I am careful about is a draw that is the same as an empty pipe. Sometimes I am able to fix this with a pipe cleaner stuck all the way into the draw hole if the draw gets too tight after tamping.
I tamp very lightly. I am not upset if I have to relight. If I sip, I can taste the top of the tobacco even at the very end of the pipe. And, most significantly, since I have started to sip, really sip, I am getting almost no backwash when I smoke. (I also tend to lean the pipe step-up when holding it.)
It seems to me, after this rambling exposition, that keeping a pipe lit is, in large part, dependent upon the ability to get air into the bottom of the packed pipe. So, by extension, getting it lit "the first time," must also be dependent upon that, coupled with the embers being in contact with the next layer of tobacco.
So, for me, it is a dance between keeping the pipe tamped, but not tamped enough to block the bottom of the bowl.
And, it is still a great deal of fun working it all out. My pipes actually have personalities at this stage of the game for me.
How cool is that?