Relights

If the tobacco has been dried out enough then I guess it is your packing or cadence. Taking slow shallow sips is good for smoking lighter blends like VA's or aros, but when I'm smoking an english I puff away with billows of smoke and don't really think about it. As long as the bowl doesn't get too hot or the flavour gets ruined then you'll be fine.
As far as lighting, I prefer matches but other people here use zippos/other lighters with good results.
For packing, if it is too lightly packed, not enough of the tobacco will be contacting to really transfer the embers down. I pack ribbon cut blends fairly tight. If I take the first 5-10 puffs and the tamper collapses the ash halfway down the bowl, then the packing was too light. Just remember that as long as you get a good unlit draw through the pipe, then you aren't packing too tight.

It is frustrating having to keep relighting, I think latbomber's given a great response. From my experience, packing too lightly creates more problems that packing too tight, so maybe pack it a bit tighter.
Again in my experience, sipping might not bring the heat and embers to the unburnt tobacco below, so try a bit more than sipping, but not quite 'drag' like for cigarettes.

So many possible variables...

Your tobacco, was it a goopy aromatic or wet flake? What sort of pipe was it? I find wide chamber pipes harder to keep lit. And, the stuff addressed by the above.
I pack mine by the draw. If I can tell that there's something in the pipe by my draw, without having to work hard to get the air to pass, that is just right for me. However, you might try one of the many "methods" for packing your bowl. Three step handshake method, the Frank method, and any of the popular methods being discussed recently. But, I think that after we get the hang of packing, many of us just do the codger scoop method after we get an idea of how tight we like it.
Me, I barely even consciously pull or draw on the pipe while smoking. I just clench it and sort of let the smoke come into my mouth on its own with my breathing. But, I just enjoy the flavor better this way. Others may enjoy theirs by making big clouds of smoke, or holding the pipe and pulling it away from their lips every few puffs. It is just a matter of finding the way you enjoy the flavor or process better for you and perfecting that method. I've actually gotten to where I will sometimes leave a pipe in my mouth for almost an hour after the bowl is finished before I realize it. It just sort of becomes a part of me.
But, all of that said, I find that if I am in conversation while smoking, I tend to have to re-light a bunch, because I am just not focused on smoking. I was doing this the other night with a buddy of mine who smokes cigars, and he made a comment about me making pipes look like hard work. Slightly embarrassed, I just stopped smoking till the conversation was over and lit it once while walking away and finished my smoke uninterrupted.

Are you occasionally using your tamper? I find that lightly tamping the tobacco down every so often will help to keep the ember going. After time you somewhat get a sense when you need to do so.

My guess would be you're either packing to lite and/or not tamping enough. Also don't puff to lightly because you may not be drawing hard enough to keep the embers going; of course you don't want to draw to hard because you don't want to scorch your tongue. Its one of those things it just takes practice of knowing when to dry the tobacco, how to pack (depending on type of tobacco), when and how often to tamp and how frequent and how hard to draw. As for lighters vs. matches I don't think that matters at all.
With all that said... I'm one of those people that doesn't care how often I have to relight. If I make it through a smoke with 2-3 relights great, but I also don't care if I have to relight my pipe every two minutes either. As long as I'm enjoying my tobacco that's all that matters to me. Good luck.

Stick the pipe in your mouth, light it, and clench it in your mouth until your done smoking. Just breath naturally through your nose, and puff every few breaths through your mouth. I'll bet you won't be relighting so often. A few relights is normal. I've probably only smoked 100 bowls in thousands smoked without a single relight. No big deal.

+1 for regular tamping. I notice that if I don't tamp every so often, then the ash buildup doesn't "collapse" on itself but rather builds up creating a barrier or insulator to air flow. Just a theory, but the tamping helps. Puff on!

As latbomber points out, if you pack too loosely you won't have a good ember. The ember has to be large enough, and hot enough, and in close enough proximity to new tobacco, to be self-sustaining. Tamp a bit more (this compacts the ember and presses it into contact with un-burned tobacco) and if that doesn't help, try packing a bit more firmly.
I like my pipe and my cigar like my women -- a bit on the loose side. But too loose has it's own problems.

+ on the tamping. The tobacco pieces, shreds, strands, etc. must be be kept in contact with each other to keep the ember going. Also, the tobacco will expand as it lights and will thrust itself upwards so an occasional tamp will keep the tobacco in contact to further keeping the rest of the tobacco lit.
Other than that, relighting is simply part and parcel of smoking a pipe and don't be overly concerned about it. This idea of lighting up a bowl with one light and slowly burning the entire bowl down to a fine ash is rarely accomplished and a pipe dream (pun intended) and certainly nothing to consciously strive for. :wink:

Packing light is great, as long as you tighten the pack up with your tamper as you go. Not heavy tamping, but regular tamping. I prefer an angled tamper as opposed to a flat bottomed one. See pic below. I tamp the circumference of the bowl with the angled end so I actually form a raised mound in the center of my bowl. Finally, run a pipe cleaner right into the bottom of the bowl and into the tobacco in the heel(through the stem of course) and you will be surprised at the change in your smoke.

Best of luck.

bullbriar, that is an awesome pipe tamper.

Thanks Wilson, I made it last year...I'd be lost without it. My father fell in love with it, so I made hime one too. What you cant see is is that in the flat end, I eembedded the cartrige rim from the first deer I shot years ago.

Of the responses above I think the one who asked if you tamped periodically best. When you light up you establish a coal on the surface of the tobacco. It will burn happily until the tobacco below it is gone and the next layer is too far away to ignite. Tamp and whallah! The coal now sits on top of the tobacco once more.
This year I've begun using my finger as a tamper. There's nothing wrong with traditional tampers, but with my finger I don't have to monkey around finding it on my smoking table and deploying it.

Of the responses above I think the one who asked if you tamped periodically best. When you light up you establish a coal on the surface of the tobacco.

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+1
As I'm a slow smoker, I'll also cover the bowl of my pipe with my fingers if I sense the ember is fading. After a couple of good puffs I gently tamp (while puffing) and I'm back in business!

My guess would be you're either packing to lite and/or not tamping enough. Also don't puff to lightly because you may not be drawing hard enough to keep the embers going; of course you don't want to draw to hard because you don't want to scorch your tongue

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+1
You're not alone drsquat. When this happens to me it's usually due to poor packing (I sometimes rush the packing and always regret it) and/or not paying enough attention to the pipe while smoking. Tamping is also very important.
And also getting a good light going in the first place.

I've just started with the pipe and I've had such a hell of a time trying to keep the pipe lit for more than 20 seconds that I just give up and dump the unused tobacco and quit for a week. I want so bad to enjoy it but it's turned out to be more frustrating than ever.
I've read how to pack it and it still mystifies me. 1st pack, like a shaking a baby's hand. 2nd pack, like shaking a woman's hand, etc. Still nothing works.
It also doesn't help that nobody I know smokes and the one's who have smoked a pipe tell me to stay away from it.

So I've been trying this whole pipe thing for a little over a year now and this thread just answered a bunch of questions that I didn't know to ask. Honestly, I feel just like shavago, no one I know smokes a pipe and the ones that have tried hate it.(Plus I'm broke and can't buy tobacco and even if I could i'd have to drive atleast an hour and a half) I really like smoking a pipe, it tastes great, and it tells people right off that I'm a little different. Which is great because I am. lol

Does anyone else use occasional "back drafts" to keep your pipe lit? That's what I do if I feel it start to go out. Just give it a few soft puffs and back it comes.