You might want to consider a couple of cobs to start with they are inexpensive and easy to smoke, they don't ghost so you can try different styles of tobacco easily.
A lot of people seem to start with the aromatics, I don't really agree with that but that's me. Being a cigar smoker you might get more out of non aromatics, Virginia/perique's, burleys and English blends. For me these are easer to light and smoke.
If you do go with the aro the Drew Estate stuff is pretty user friendly.
You will need pipe cleaners and a tamper, for the cob pipes don't forget to pick up filters, the paper ones are fine.
Check out the how to video's on you-tube, ask lots of questions. Smoke very, very slowly, it's okay if it goes out a few times.
Contact Sean at Ccom he can and will help.