New to pipe puffing... possible n00b mistakes?

My guess is that the tobacco is too wet. Dry it out for about 1/2 an hour and try again. Other will be here shortly to offer additional advice.

Welcome to the forum. Like anything else worth doing it takes practice, practice, practice. Don't be discouraged; we've all been there and many of us before the internet was available.

I've copied a site below from James Fox Tobacco of Dublin. Great little videos on loading and lighting a pipe.

Also, you've come to the right forum. The collective knowledge and experience here is incredible.

There are no dumb questions and you'll always find someone to help you.

So rather than me writing a lecture, watch the video and then practice and then ask away.

I hope to see more of you here.
http://www.bing.com/videos/search?q=james+fox+pipe+videos&FORM=VIRE1#view=detail&mid=141516F30609D0B9D464141516F30609D0B9D464

First off welcome to the pipe world and to the forum. Like zitot said let your tobacco dry out a little before you pack it, and like pipipeguy said just keep practicing. I will also add in that when you pack your bowl fill it 3/4 of the way pack it a little harder, then fill it the rest of the way and pack it again lighter, and also don't draw to fast or hard or you will pit the pipe out.

Don't get too discouraged about the cigarette smell - there are some blends that more closely match cigarette tobacco (I've found that Sir Walter Raleigh is one that I can't smoke, as it's far too close to cigarette smoke for my tastes), and others that both smell and taste remarkable.
As you've already found out, there's often a significant difference between the way a tobacco smells in the pouch or tin (particularly an aromatic blend) and the way a tobacco smells and/or tastes when lit. Non-aromatic blends are generally closer in aroma/taste profiles, but you'll find some aromatics that do maintain some of their scent while being burned.
If you can find a tobacconist that allows sampling of their bulk blends (often kept in jars - my local B&M does this), take advantage of the opportunity. If not, take a look at some of the online vendors (several of whom are site sponsors, linked on the left side of the page) and buy some 1 or 2 oz. samples of blends that either sound good or get mentioned favorably here in the forums. Eventually, you'll find blends that taste/smell like what you want to be smoking, and you'll develop your smoking technique so that the experience becomes the calm, meditative practice that so many of us go on and on and on about... :wink:
Oh - and don't sweat the relights. A lot of pipe smokers refer to the initial application of fire to packed tobacco as the "charring light" or the "false light", as it doesn't actually stay lit, but instead chars the top layer, allowing the second application of flame to create the smoldering "cherry" that burns its way down to the bottom of the bowl as you smoke. If your tobacco is pretty dry, your charring light may well create a cherry that works - but more often, you'll find yourself lighting another match or clicking your lighter several times per bowl, especially at first.

My hints for new pipe smokers:
1. The tobacco should be a lot drier than you think it should be. (Almost crinkly. I mean it!)

2. The tobacco should be packed a lot looser than you think it should be.

3. The pipe should be smoked a lot slower than you think it should be. Sip--don't puff. The pipe should feel comfortably warm in your hand. If it's hot, you're smoking too fast.
Here's another hint: if you want that delightful smell, hire a guy to smoke it for you, and sit back and enjoy the aroma. If you stick your nose over the bowl and sniff, it will taste very similar to a cigarette. It is, after all, burning tobacco. Give yourself time. Pipe smoking is an art, one that is carefully cultivated and learned, bit by bit. In time, you will develop your tastes for certain tobaccos, you will develop and refine your smoking technique, and you will come to enjoy one of the greatest pleasures that God has provided us. Patience, my friend. And read your way through this forum. There's much to learn on your way to Pipesmoking nirvana.