I'd take your time to peruse some of the expansive retail sites like our sponsors smokingpipes.com, iwanries.com, pipesandcigars.com, cupojoes.com, and 4noggins.com. Just do some of each site at a time, a brand or two, and hold off on buying until you begin to get a feel for what's available, at what prices. Get a feel for filters and non-filtered pipes, and how you want to proceed with that. The best cob brands are Missouri Meerschaum and Old Dominion, in my opinion, and these are inexpensive and excellent smokers, and will give you a rotation, to rest your pipes, while you learn more. Really take your time with this. A few cobs would give you plenty of pipes to buy time to learn briar and Meerschaum pipes, and a little about other woods that are used. With tobacco, don't buy more than a tin, or an ounce or two of anything, until you really learn what you like, and what you continue to like. The more deliberate you are, the fewer mistakes you'll make, the more you'll enjoy the trip. I'd buy new pipes for the first five or six, so you can stick to dependable products likely to be pleasing, before you venture off into estate (used) pipes, if you do that.