Hi Scott, and welcome out of the shadows!
You can't go wrong, either way - let your budget decide. Having experience with all models, except the #4, I'll throw in my 2ยข. I started out with the #1, since I didn't know anything about Smokin-It back then, and it was to be my first "true" smoker. I couldn't justify the larger #2. At that time, the forum was very new, and there just wasn't the input there is today. I got the #1, and my first impression that it was built very well, but seemed much smaller than I thought it would be. As Kari said, you can do one pork butt at a time, 3-4 racks of ribs, one whole chicken or turkey, but I differ in opinion on brisket. Yes, you can fit most brisket flats in there, but if you want to smoke a full packer cut (point and flat), you will have to cut it in half and put the halves on 2 shelves. Doable, and I've done quite a few of them that way, but it kind of defeats the purpose of a full packer (imo).
Did I regret getting the #1? To be honest, yes. Almost immediately, in fact. Once I saw the quality, and got a few smokes under my belt with it, I knew I'd made the wrong decision on the size. I thought, at the time, there's no way I'd EVER need a #3, but I'd sure like a #2! When the #2 arrived, I fell in love. The specs, on paper, don't seem that much bigger, but it is. More height, width and depth. I could fit a reasonably-sized packer brisket in there! 2 butts at a time, if I wanted, too! Ribs still had to be cut in half, but big deal. Love the #2, and still use it today. The old #1 is only used for some side items, and occasionally at that.
Enter the #3! Got my hands on the new 3D, and Wow! Although I only regularly smoke for me, my wife and son, you just can't underestimate the Q real estate offered by the #3. There are no limits! If you want to smoke really big briskets, you can! Multiple butts for a party, or event? Oh yeah! I don't know about you, but if I need 3 pork butts smoked for a group outing, I don't want to take 3 days to do it! I know you've seen this statement, but I can't emphasize enough that you can always smoke less in a 3, but never more in a 1 or 2.
Bottom line? Let your budget, and needs, make the decision. Personally, I wouldn't go smaller than a 2, but would get a 3, if able. Bigger is not always better, but in the case of what is really a "lifetime" smoker purchase, it is.