Words of advice I have given successfully to many starting out:
1. Buy a Weber 22" Kettle Grill
2. Buy Thermopen
3. Buy B&B Lump Charcoal - HICKORY @ Academy w/ chimney starter
4. As stated by ReinerAg09, pick one cook.... hamburger (85/15 or 80/20), chicken breast, then pizza, etc. and master that. For working folks, 3 to 4 months to master when you have time is a good estimate.
5. Once you master several items as discussed above, buy a Smoke N' Sear insert and use that until you feel comfortable. Then, if you want to buy a real smoker, not an outdoor compressed sawdust oven, GO FOR IT!
Folks might not be in agreement over the steps above, but I'm a 3x Texas A&M BBQ Camp attendee, trial and error before the intranet, listened to alot of experts at camp, pitmasters and put it into action at home...I don't comment much on BBQ threads because 75% of the folks don't know as much as they think or are self-proclaimed pitmasters using a pellet "grill" oven. LOL
Good luck and Godspeed!