Starbuck,
I smoked cigars for years, and never a pipe. It was Jack and Linus who got me really interested in pipe smoking - plus I got my Grandfather's pipes after he died. So with that said, what I did is this.
I went to a cigar/pipe/tobacconists shop in town. I went in with a pipe, and sat down at the pipe lounge. I asked the guy behind the counter a ton of questions about the tobacco. Jack and Linus helped me with the tools and how to clean out a pipe.
I think taste is personal. Some enjoy certain flavors when it may not be so good to others. It is just a matter of what you enjoy. Most places will be happy to give you a pinch to smoke before you purchase any tobacco. I say get a pipe you like, and go to a local shop. Don't be shy. Ask questions.
Smoking a pipe is very calming to me. It slows down my OCD. It gives my hands something to do while smoking. Cigar smoking is faster than a pipe. I still enjoy both.
Let us know how your smoking journey goes! Have fun!
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