Get a pipe tool with a tamper. Then tamp the tobacco down in the bowl as it's smoked. This keeps it lit, but also keeps the tobacco burning to the bottom of the bowl.
You can smoke a pipe two, three, even four times a day, but you need to keep the heel from getting wet.
NEVER take a warm pipe apart -- regardless of what sort of bit it has. Moving the bit in the hot shank can break the shank.
When I'm done with a bowl I stir up the ash, hold my thumb over the mouth of the bowl and coat the interior of the bowl with white ash. This helps develop a cake inside the bowl. Also, the dry ash helps dry the interior of the bowl.
Run a pipe cleaner down the stem and shank, into the bowl. Turn the cleaner end for end and run it again. Then set the pipe with the stem facing up so the moisture in the stem can run into the bowl and evaporate.
Smoked pipe should get to "rest" for a few days. A week is nice. Seven day pipe sets are made with this in mind. Most smokers have several pipes. I rarely smoke a pipe more than twice in a day.
If your pipe is getting a damp "wad" in the bottom of the bowl it's time to clean it and give it a rest -- more than time actually.
Breaking in --
Dust out the bowl with a damp cotton swab, remove the factory and shipping dust. Run a moist pipe cleaner through the stem for the same reason. Water is fine. Bourbon or brandy is nice if you have some. Personally, I wouldn't waste the liquor.
Small pinch in the bottom of the bowl and smoke it completely. Let the bowl cool before smoking again.
About five smokes and then 2/5 and five smokes, 3/5 bowl and five, 4/5 and five, and finally fulll bowl. Don't rush!
You want to build a cake in the bowl from the bottom to the top. And you want the cake dry and hard, not gummy, wet.
Get a decent pipe lighter and learn to light the tobacco with the flame. Don't flame the top of the bowl. I see pipe bowls that are scorched and burned away from lighting.
There are books out on pipe smoking. They're worth reading. Pipes and tobacco are nice to smoke and relaxing if you're willing to learn how to care for a pipe.
Most pipe smoking books discuss tobaccos, and that's a whole world unto itself.