I suggest a pipe or two (I started with briars but MM cobs are much cheaper and smoke great) and a variety of tobaccos. I highly recommend 4noggins.com if you don't have a local B&M to go to (4noggins is my go to). 4noggins also allows you to order their bulk blends in 1oz (vs 2) which allows you to try a wide variety or tobaccos cheaply. I'd recommend trying a variety - aromatics, English/Balkan, Virginia, Virginia/perique, burley - to get an idea of different tastes and then using tobaccoreviews.com to read up on different blends to find similar blends with the flavours/tobaccos you enjoyed.
When I first started smoking a pipe about 4 years ago I didn't know how to pack a pipe or smoke it, or what tobaccos I liked and was disappointed when I started. After reading about flavours and nuances in different tobacco reviews I got none of it and was disappointed but I had quit cigs a few years prior and was looking for an alternative to dipping. It took awhile but now I can enjoy the different blends and flavours.
I don't smoke everyday but when I do I enjoy it. Good luck, read the forum, stick with it, and enjoy!