Welcome aboard bl20! You've come to the right place!
For starters, let me suggest that you purchase a couple of Missouri Meerschaum corn cob pipes to help start a good rotation of pipes. They're extremely cheap, they smoke great, and they don't need much rest between bowls.
As for a good pipe, save up a little money and look at Nordings, Savinelli, Stanwell, Peterson, or Butz-Choquin. Any of these can de had for between $75-$150.
For tobacco, I'd suggest getting a couple of blends from all the different genres, try them and see what you like. You don't have to get them all at once, take you're time.
Here are some suggestions;
Burleys
1) Scotty's Butternut Burley
2) Boswell Premium Burley
OTC's
1) Carter Hall
2) Prince Albert
Virginias
1) Mac Baren Virginia Flake
2) McClelland Deep Hollow
Aromatics
1) Lane 1Q
2) Sutliff Molto Dolce
Va/Burs
1) Mac Baren Navy Flake
2) Mac Baren Roll Cake
Va/Pers
1) Dunhill Deluxe Navy Rolls
2) Peter Stokkebye Luxury Bullseye Flake
3) Orlik Golden Sliced (more like a straight Va to me)
Slightly Aromatic Va's
1) Mac Baren Vanilla Cream Flake
2) Peter Stokkebye Luxury Twist Flake
English/Balkan Blends
1) McClelland Blue Mountain
2) Dunhill My Mixture 965
English Hybrid/Crossover Blends
1) All Of The McClelland Frog Morton Blends (5 total)
2) Hearth & Home Mazatec
Kentucky Dark Fired
1) Mac Baren Old Dark Fired
Some of the blends I mentioned are flake/coin stye tobaccos. They can be a little intimidating at first, but take your time, and research how to prep and pack them. Once you get the hang of them, they're no problem at all! They're are plenty of links on this site about smoking flakes, tamping technique, packing different styles of tobacco, lighting steps, smoking cadence and so forth.
There's a lot to learn, so don't overwhelm yourself with trying to be perfect all at once. It takes time and practice!
Good luck, and feel free to ask any questions you might have!
Dan