No judgment on too loose or too tight, but you may want to give this a whirl, it's how I learned:
Pack a pipe like you would normally, then dump out all the contents onto a paper towel or napkin and take about 1/4 of the amount away from this small pile and put the rest back into the jar, tin, pouch or bag. Use this 3/4 pile remaining to pack your pipe.
While it is on the paper towel or napkin, it may be be advantageous to ensure it's dry to the touch, not dry to the point of crumbling, and not moist to the point of clumping together when you pinch the tobacco. The amount of moisture may be inhibiting an even burn too...so until you find your own level of desired tobacco moisture, you may want to go more on the drier side for the tobacco you are putting into the pipe.
Then, repack your pipe with the 3/4 amount on your paper towel, going loose toward the bottom, making a very fragile nest inside at the foot of the bowl. Then apply the next layer, press gently with your tamper or your finger, being very economical with the amount of pressure. Alternate packing and tamping (I still rely on the three layer or multi-layer method) until you are out of your pile or you reach the top.
The tobacco should be just about at the rim and yield a springiness when pushed down with your finger or tamper. Put the stem in your mouth, give a test draw. If it's too loose, there will be zero resistance...too tight and you'll hurt your cheeks, just right is like sipping a soda through a straw. Here's an ideal time for a note of caution: Too loose and you'll get tongue burn.
Perform the charring or false light...this step is generally complete when most if not all of the visible tobacco seems blackened and you're getting a pretty good amount of mouth smoke. Some tobacco may "poke" out over the rim just a bit as it becomes charred. That's okay. After noting or observing the right amount of char, let it go out.
Now, just ever so gently, crush the carbonized tobacco on the top, twisting just a little, using just a little more pressure than you would if trying to remove an eyelash the eye of a loved one. The tobacco should be just below the rim.
Re-light, making sure to bring the source of flame all around the circumference and middle of the tobacco and gently draw while it's lighting. Drawing or "hooting" too hard, and you'll get tongue burn, perhaps a follow-on gurgle, and at times an unpleasant taste. The key here is to slowly sip, especially if you are smoking a heavily cased or virgina based blend. Also as an aside, slow and steady may prevent burnout (the walls of your pipe begin to burn). For me, I tend to draw every eight to ten seconds or so, and I learned my best rate by not keeping the pipe in my mouth. I held it in my hand until I developed the right drawing tempo, only then would I clench while typing or driving, etc.
When to tamp? If you'll notice, at first you'll have a good amount of smoke, and as the tobacco burns, you get less and less. Right before the smoke get's thin and wispy, here is where you tamp. But go lightly at first, gently crushing and slightly, ever so slightly twisting the tamp to ensure the burning portion or embers are lightly distributed and introduced to the amount of unburned, but warming tobacco below.
Go slow and monitor your rate of draw. For some, they smoke a pipe like a billows, and hey, that's cool. But starting out, I found it best to follow the above routine to keep the pipe a-fire. When relighting, tamp gently, then introduce flame, draw, and sip.
In closing, a pipe is like a murmured whisper while a cigarette or cigar is like a shout. It's okay to re-light and you'll see, as time progresses, you'll get better and one day, have a complete pipe consumed with just two or three lights. Slow, steady, patience and practice and I think you'll see the flavor obtained from each smoke is better, more complex, and something to savor, while making the pipe what it's meant to be, an experience.
Later,
Archer