Hey- welcome to our little corner of heaven, SadiumSax! I also suggest trying a corn cob pipe, as they're cheap, simple, and "good enough" for a starter pipe. Posted in another thread, pstlpkr suggested testing pipes with a pipe cleaner before buying, and rejecting anything you can't get the cleaner through easily (pipe stem to bowl), and I think that's a wonderful suggestion.
As far as tobacco is concerned, its all subjective, so eventually you'll have to try many different kinds of things to get a handle on what you like. I strongly suggest you stick to buying pouches or small quantities of bulk tobacco until you get more of an idea of what you like. Few things suck as much as reading the ADVERTISING copy on a can of pipe tobacco or web page, shelling out the $$, and getting it home and finding out it smokes and tastes like a three year old gym sock you lost... in your basement. Before your basement flooded. Twice. I'm just saying- buy smaller quantities so you don't end up with a mountain of unwanted pipe-weed.
There are MANY different variables that go into a pipe tobacco:
Types of tobacco:
Virginia, Burley, Cavendish, Latakia, Oriental, Perique... more. I have found that I really dislike Burley, but love Virginia and Latakia...
These can be cured in various ways:
Air Cured, Flu-cured, Fire-cured, Steamed, and more. This will change the way a tobacco tastes.
These are all combined in various ways to create (or not) mixtures/blends:
Aromatics are sweeter and smell nicer to you and people around you, but often have flavorings (which you may or may not like) that mask or enhance the tobacco.
English Blends can be almost anything, but usually contain no special flavoring agent and do contain Latakia tobacco, a special type.
Danish Blends Uh... I don't know what makes something a Danish blend, I just know (or think I know) that its a style... anybody help me on this one?
Then they can be "finished" in various ways: Riff cut, fine-cut, ready-rubbed, ribbon cut, flakes, cakes, plugs, twists... Though I recommend sticking with "Ready-Rubbed" until you learn more about those others.
... In the end, you'll have to try a little bit of everything. But don't let one bad bowl ruin a nice hobby; you might LOVE the next bowl of something you try!
Recommendations?
For a Pipe:
A good starter pipe might be a Missouri Meerchaum (Corncob), or a Dr. Grabow, which I like better than Kaywoodie or Medco.
A better quality pipe I can recommend without reservation is a Savinelli, specifically from thier "Duca Carlo" line- run you about $60 online. I have 2, and I love them. Don't be frightened by the different "filter" system, its a good pipe.
For Tobacco:
Drug Store Blends: Prince Albert, Middleton's, Captain Black Royal (Blue)
Mac Baren "Mixture" (Scottish) and Vanilla Cream
GL Pease Westminster or Chelsea Morning
Good luck! Let us know how it goes!