That is all part of "The Ritual". Improving one's technique takes time. Although the learning curve seems to been shortened by forums on the Internet. Different blends, how the tobacco is cut, processed, and most importantly how you like it to taste, all effect your technique.
I can tell you that I seem to like certain English/Balkan style blends a bit drier. Nightcap for me is magic when it's nearly dry as a bone. Raven's Wing can feel moist. Sort of dough-like. But then packing is affected too. I will press that dry Nightcap quite a bit into a bowl. Raven's Wing gets a very light pack. Just more to fill most of the space. Then I let the tamper lightly do the rest.
I think we learn and make judgements when we examine the blend. Then modify our technique over a series of bowls. You read about people like me, jumping from blend to blend. Always something different. I think we, I, learn slower sometimes. Slower than the fellows who open a tin and smoke only that blend until the tin is gone. They perfect their technique quicker I would think, for that blend. I would assume their pipes get seasoned for a particular blend better. Someday I will see if that enhances a blend by smoking only the one blend, and only in a few pipes, till the tin is empty.
I agree with Carlos. "Its the journey" that matters. I find that some of the English blends are quite moist out of the tin so I let them dry a bit then put it in the mason jar. I like the tobacco on the dry side. If it is a flake, I fill the bowl with broken flake and put the powder on top for "kindling." Penzance I age and let dry some and pack very loosely. It is all experimentation that led me to this.
I've had great luck with extra-dry tobacco. Kind of crunchy on the tamp sometimes, but holds a light well, full-flavored, and clean burning.
The first experience I had with the extra-dry tobacco was with an old tin of Royal Yacht. This stuff was dustbowl dry. I thought about rehydrating it, but decided to smoke some just to see. It wasn't bad. From there I try it with new tobaccos bowlfuls at a time.