I smoke one cigar a day, and a pipe every once in a while since 1973.
Be aware of healh hazards, a search on the web will bring up lots of info, unfortunatley there isn´t much research done about cigar and pipe smoking, however, everyone seems to agree that if you inhale you are just as bad or worse as with cigarrettes, if you smoke a pipe, enjoy the flavor and don´t inhale, it is a good idea to change the side of the mouth where you smoke the pipe, and rinse your mouth after smoking.
If you don´t smoke more than once a day you shouldn´t need more than one pipe, but it´s nice to have several (I have more than 50), I´m partial to Peterson´s standard system pipes, I feel they smoke nice and cool, I have 4 of them and they are the ones I always pick up.
I suggest you just drop the tobacco loosely to the rim, then gently push it about halfway down the bowl, drop some more loosely to the rim then gently push it 1/4 th down, with time you´ll learn to pack fine cut or dry tobacco a bit tighter, thicker and humid a bit looser.
Light the top of the tobacco evenly while puffing very gently, make sure the whole surface gets lit, take your pipe tamper and put it off without pushing, light it up gain, do this 2, 3 or 4 times as necessary so that the tobacco is burning evenly.
It takes some practice to smoke properly, puff too hard and the pipe will overheat, puff too soft and it will go off, use your pipe tool to keep the tobacco packed evenly and not too tight or loose, be aware that a layer of ashes is being formed as you smoke which prevents air from getting to the unburned tobacco. Handling all this is part of the smoking ritual and it takes time and practice to get it right.
After smoking, let the pipe cool down and clean it, if you don´t your next smoke may be bitter, some people leave a pipe cleaner inside the mouthpiece when the pipe is not in use.
There are many varieties of pipe tobacco, you may have to try around until you find one you really like.
You have gotten good advice here from other forumites, and there´s plenty of info around the web if you look around.
Enjoy responsibly.