Problems with my pipe experience

Fairly new to this myself, but had some luck with packing.
Don't worry about relighting - it depends on how you smoke, tamper etc. You might be packing too tightly, so next time try to pack more lightly and see how this feels.
about the flakes - had a few of these myself, and I don't see a way around it. It happens at the beginning and stops when the tobacco "settles" in the bowl (usually after I light the True Fire).
Those are my 0.02...

But again - I'm very new to this myself :]

I started smoking a pipe about 10 months ago and for what it's worth, it took me a good month or more to get a handle on how to pack a bowl correctly. It also took a while for me to understand just how to actually 'smoke' a pipe, how to draw on it, and at what pace to do so. A lot of this will come with experience as everyone has a different approach. That being said, the goal is a cool, dry smoke. I've found that the slower I draw (not by inhaling but by closing my mouth around the pipe and just lowering my jaw to pull the smoke into my mouth) the better the tobacco tastes. I can really pick out the nuances this way.
You will, with time, get the feel of how dense or loose you'll want to pack your pipe. This will differ when and if you get in to flakes. For the most part, a bowl that is too tightly packed will have a hard time keeping lit as oxygen won't be able to reach the ember easily. This can result in a very hot, wet smoke. I'd rather err on the side of too loose as I can tamp down the tobacco as it burns, tightening it up as I progress down the bowl.
As an alternative to the 3 pinch method, you might want to give this technique a try. It has worked for me:

https://www.youtube.com/watch?v=0XHYPso7TXs
Good luck on your journey. It only gets better.

I will have to look at that link, thanks! I also wasn't sure if you should tamper down as you go, but I can try this as well.
I'm not giving up on this yet!

Click to expand...

Good. Don't give up. While smoking a pipe isn't all that complicated, it takes some patience and practice to make it easy.
I'm a relative newcomer myself. I've only been at is for about 45 years, off and on, and I'm still learning things.
So here are a couple of thoughts. Don't overthink it. There are different ways to pack a pipe and they all more or less work. However you do it, you should be able to easily draw air through it.
Tobacco moisture affects lighting and flavor. Most tobaccos have more moisture, in the tin, than is optimal for getting the best flavor out of it. Give your tobacco 20 minutes to dry, spread out on a plate, before you pack your pipe. Proper moisture content, like everything to do with pipes, is a matter of debate, but what works for me is that the tobacco feel dry to the touch when squeezed, but still pliant. It shouldn't be brittle.
Pack your pipe so the tobacco is springy and semi firm, apply a soft flame to it (zippo, BIC, match - no torches!!) and puff a few times while moving the flame over the surface of the tobacco, to get the tobacco burning and to char the surface. Let the tobacco go out and LIGHTLY tamp the surface to create a thin layer of ash. This is called the charring light. It used to be canon. Now a lot of people call it bullshit. You decide as you progress.
Relight and take a few puffs while moving the flame over the surface. Once the tobacco is going, stop puffing and start taking nice slow sips of the tobacco. You get the best flavor when the tobacco is just simmering around the coal. Sipping provides enough draft while not overheating the tobacco. It the pipe goes out, relight and continue. It takes some practice to get the feel of how this works, but practice makes it all pretty easy to do.
Don't worry about relights. Everybody, except me, has to do them. I'm perfect. But really, don't worry about relights. Also, don't worry about cremating every last shred of tobacco in your bowl. It's better to toss out the last bits.
Smoke slowly. If your pipe gets hot, slow down a lot, or stop and let it cool down. Don't smoke your pipe like it's a furnace.
That's plenty for now.

I, like many, had similar problems in the beginning. I found a different method (a "stuff" / "air pocket" hybrid method) and found a great article about the Thermodynamics of Pipe Smoking (which is no longer available anywhere on the net). That article discusses the benefits of lighting only the center of the tobacco, albeit not in exact terms. (Not to worry, the entire bowl will be smoked.)
As for my packing method, I experimented and failed for quite a while. And, I literally have scars on my tongue as evidence of my failures. That said, I read, and watched videos, and found my way.
You will find yours. I know this because you are "not giving up."
Happy experimenting.

My method involves shoving tobacco in, smushing, shoving more in, smushing.
It probably looks haphazard, but I'm sure it's muscle memory making it look/appear more simplistic than it might be.

I, like many, had similar problems in the beginning. I found a different method (a "stuff" / "air pocket" hybrid method) and found a great article about the Thermodynamics of Pipe Smoking (which is no longer available anywhere on the net). That article discusses the benefits of lighting only the center of the tobacco, albeit not in exact terms. (Not to worry, the entire bowl will be smoked.)

Click to expand...

That article was on the now closed site A Passion For Pipes. I have a copy of it.

I don't know what pipes you have, but I recommend buying a new Savinelli. The pipe does make a difference. If you have a pipe that smokes hot or wet it will affect the flavor of your tobacco. I am not a fan of smoking dry tobacco, to me it burns hot and it loses flavors very quickly. I always smoke my tobacco on the moist side, I get way more flavor that way.
Pipe smoking is an art, it takes time to learn how to smoke a pipe. Don't lose patience, it might take a few months or more to get good at it. Read everything you can and keep asking questions here, this is what we are here for.
It took me over a decade to finally figure out exactly what I want in a pipe. I match my pipes to smoke certain types of tobacco. For example, I smoke flake tobacco 95 percent of the time. When I am looking to buy a pipe, I ask myself how well will this pipe smoke my flakes, I have strict criteria as to what I want in a pipe. I want a pipe that weighs between 40-60 grams, depending on straight or bent. I want a bowl size approximately 2 inches tall with an inside bowl width at .75-.82. I want a inside bowl depth to be around 1.45-1.75. I want the inside shank dimension to be around 4.0-4.5 mm. I like a pipe that is 5.0-6.5 inches long. I buy hand cut stems made from the finest German vulcanite. I buy certain shapes and some would call me boring as they are all traditional shapes i.e Dublins, Rhodesians, Apples, Billiards, Lovats, Brandy's, Cherrywoods, Zulu's.
This criteria took me a hell of a long time to come up with. When I began smoking a pipe, sites like this did not exist. It was trial by error and there were a ton of errors. One site I did have is tobaccoreviews.com. I learned a lot about tobacco and I found reviewers that had similar tastes to mine so I would try blends they liked. On this site we have the 2 most prolific reviewers on that site jiminks and pipestud, check their reviews and see if you can find some similar tastes.
Pipe smoking is a journey, it is not a race.

mike', plenty of good recommendations here to help you along. Mainly, relax and fiddle around with it. Good things will happen one at a time. Packing the pipe just a bit tighter (but so it still draws easily) might keep the tobacco from drawing up the stem. Nightcap is a good rich blend, so lack of taste is from working too hard at the mechanics and not sitting back and letting the flavor develop. Don't try too hard. This is a pleasure and a relaxation. If it isn't working one time, leave it and come back later or another day. I think you'll begin to discover the pleasing parts as you go along.

Pipe smoking is an art as much as anything, practice makes perfect, each pipe and tobacco blend have their own characteristics that you will learn over time, just take your time and think through each issue as they come, many hear will help guide you to an enjoyable smoke.

My pipe journey began in 1976, so I have only been at it about 40 years. Depending on the cut of the tobacco and the size of the draft hole, I occasionally suck up a peice of tobacco. It comes with the territory! I like pipes with a 4mm draft hole, so I try and avoid the tiny peices whe packing, or use a filtered pipe. Many of the blends I enjoy smoke better for me with the 9mm filter. Don't be discouraged, however, because as you learn cadence and sipping of the smoke, frequent relights will become unnecessary.