Pipe smoking (Tobacco)

[Jihad]

I've been enjoying cigars for about 10 years now, and I really enjoy finer tobacco products. Since the first time I smoked a pipe when I was around 16, I've always had a small infatuation with the idea of smoking a pipe. The problem is, I can't get over the image that comes with a pipe. I am, like the rest of us, at least a little image-conscious and the image of a 75 year old man talking about "The War" while asking you to speak louder is not really something I'm going for.

Recently I added a patio to my home and that has rekindled my desire to become a tobacco pipe smoker. My fiance thinks its absolutely ridiculous, as do a few of my friends that I've polled, but I've decided that I don't care and I'm going to go ahead and buy a pipe.

This brings several questions to mind, as I am completely new to the scene. I have found an excellent tobacco house here in Jacksonville in terms of their selection, but they are not all too friendly or helpful, especially when it comes to their pipes. I'm in the market for something in the $100 range, I'm willing to fudge either way if something suits me, but I don't really know what I'm looking for with regards to quality or even brand recognition. I also don't know if there's any method I should be using for choosing tobacco other than the "ooh that smells good" approach.

So do any of the ElD readers have pipe tobacco experience? Is the idea of a 27 year old man smoking a pipe just too much to overcome? What kind of pipe should I be looking for, and what kind of tobacco do you buy/like? Thanks.

-Jihad