New Pit - Weber Smokey Mountain
If you are a reasonable and intelligent person you would start off a new hobby by going small and taking the beginner route. I am far from intelligent and reasonable is not my strong suit. My first pit, and one I still use, is a monster. With the capacity to cook a 200lb hog and still have the space left over to handle another 100lbs or so of meat, it's larger than what anyone needs. The fact that it sits in New York City makes it even more ridiculous.
My smoker is an offset smoker. This means that I burn wood on a box end and the heat and smoke feeds through the rest of the barrel and cooks the meat. Learning to operate an offset will break most people. You heard about people cooking at 225 degrees for X amount of hours? Well that isn't happening in an offset. Burning live wood means that you deal with temperature spikes and drops. You have to figure out how much wood to burn and how often. My first few runs with this darn near killed me.
I know how my pit works now and it's hard to imagine NOT cooking with only wood for me now. But as the Fall hits and occassionally I DON'T want to smoke a few hundred pounds of meat at a shot, I needed something more reasonable.
When a hardware store had a clearance on their floor model for a Weber Smokey Mountain 18.5 I jumped on it. The 18.5 WSM is the PERFECT beginner's smoker. The instructions are really simple to follow and there's really no spikes in temperature. The downside is that you can basically leave this alone without tending it. For me, most of the fun was tending the fire. Controlling your fire is a skill you only learn from cooking with live wood.
The best thing about the WSM is the sheer amount of resources available for it. Weber the brand has been around since 1893 and their products can take a BEATING. I still have my original Weber charcoal grill from 5 years ago. I just polished her up yesterday and she looks brand new. While it's a beginner's grill it's used at the highest levels of competition. Harry Soo is much lauded BBQ champion and is known for beating out $20,000 rigs with his simple WSM set up. To be fair though, most of the expensive rigs are more about the ability to sleep in comfort than they are about cooking prowess.
My Buddy's BLOG - Josh blogs and competes with the WSM so his site's a great resource.