Greg pretty much hit the nail on the head. I started with cigars and switched to pipes. Now I won't hardly touch a cigar. I also started with a Briar and it didn't hurt me any, if you are like most of us just one pipe won't do anyway
. The flavored tobaccos you refer to are most generally known as Aromatic tobaccos they "usually" have some sort of topping to make them taste a little sweeter i.e. Maple, berry, or some form of liquor. This is fine because there are as many or more non-artificially flavored tobaccos out there, even some blends with cigar leaf. My suggestion to you in terms of tobacco is to sign up for the "Newbie Sampler Trade for Pipe Tobacco, it will expose you to a few different blends and types of tobacco to help you get started if you do decide to pick up a pipe. It is found here.
http://www.cigarasylum.com/vb/showthread.php?t=9168
Regarding pipes, the scope and spectrum is near as vast as tobacco, this may be why most of us get hooked on pipes so easily an quick. Corn cobs are good work horses you can burn em up and throw them away, they are also quite forgiving to the new smoker. That said it's hard to beat the smoke from a good and well broken in Briar. You can find a very good smoking pipe from Savinelli, Stanwell, and Peterson ( I would recommend staying away from the System Standard).
I think Curly Cut may have made pipe smoking sound like some sort of cult and it isn't quite a few people just fill up any old pipe and puff away, however the casual pipe smoker is not common and the intricacies of a pipe are almost as addicting as the actual smoking of a pipe. tobaccoreviews.com is a great website where people can rate and review different blends it has helped me quite a bit.
Cheers