As far as filling and lighting are concerned, try them all. Whichever works best for you is the way you should go. Remember to have patience! Pipe smoking can be a bit troublesome at the beginning, but once you get the hang of it, it is quite rewarding.
As far as tobacco is concerned, there are many places to get tobacco. I usually use pipesandcigars.com, but there are others I am sure people will suggest.
If you want to keep your tobacco fresh, store it in large mouth ball jars. Don't put any tobacco or smoked pipes in your humidor, for the same reason one would separate infused from non infused cigars.
A lot of questions have been answered here:
http://www.cigarasylum.com/vb/showthread.php?t=6366
Look through it and you find answers to questions you never thought you had!