Welcome Tyler. I'm currently in Connecticut, but have called Orillia and Winnipeg home. If you're anywhere near Montreal, stop in at Blatter and Blatter--one of the finest B&Ms to be found. In addition, they make their own pipes and blend some first-rate tobaccos. Please feel free to ask questions because you'll get all kinds of good advice. Some of the online retailers sell samplers that will allow you to try a variety of tobaccos. First thing is for you to decide on a general type of tobacco that satisfies your taste buds, and then begin exploring from there. Do you like English? Aromatics? Burleys? Etc. And start with a medium strength tobacco and work your way up or down from there. Pipes? The woods are full of them. Stanwell, Peterson and Savinelli are excellent and reasonably priced production pipes.
Again--welcome, Merry Christmas, and happy smoking.