Smoque, I've never seen free shipping, and not sure we will (quite a bit of money). As to your other question...it all depends on the level of "involvement" you want. Traditional stick burner folks, competitors and the like, love the process of cooking their Q. They love tending to the smoker every minute, staying with it, monitoring its every breath (so to speak). I don't, but love good BBQ. Also, only you know how much you like smoked foods, so factor that in, too.
When I decided to take the plunge, I thought the same thing. I'm pretty darn good with my old Weber gasser, and I just don't know. Well, let me tell you, it was the best "cooking" decision I ever made! The simplicity lends to use. With traditional smokers, there's lots of preparation, and then tending while it's cooking. With a Smokin-It unit, it's set and forget! The only real "prep" work is on the meat! A couple sheets of foil for the smoker, a little wood (and I mean a LITTLE) in the smoke box, and it's ready! No preheating, no fiddling with charcoal or wood until it's "just right;" this is truly "plug and play!" Meat in, set the temp, remotely monitor (with a thermometer like the Maverick ET-732), and pull it out when done! My cook time starts when I close the door and set the temp, and ends when I open the door to remove the food!
I now use mine almost every weekend, and sometimes twice in a weekend! Cleanup is easy, and so is the smoking! I call this "Lazy Q" at its finest!