Others have already mentioned these points but they can't be stated enough:
1. Buy an estate pipe from Frenchy (
http://www.frenchyspipes.com/). If it's your first order he'll usually throw in a free cob, pipe cleaners and a tool to get you started.
2. No break in period with an estate or cob.
3. Get some newby samplers to try out different blends. If you do decide to try the Captain smoke it in a cob to avoid flavoring your briar pipe.
4. I just use run of the mill wooden matches and also have a dedicated pipe lighter.
Hope that gets you started and don't give up. It took me many months of on again off again pipe smoking before I finally "got" it.