Bill, great advice. It is very encouraging to me because I have a few "dreams" and side projects that involve craftsmanship - I'd be happy to pursue any of them. But, they definitely aren't the easy road... It's nice to hear from someone who has taken the path less travelled and has emerged all the better for it. (Beekeeping is actually a hobby I have considered when I get some of my own land but I have been discouraged by the harsh climate around here - I love mead)
As far as growing your own tobacco, I've thought about it just for its own sake but I'd go into it knowing that you would very likely lose the entire batch to pests, mold, rot, or some other calamity somewhere from the farming to the curing process... Still, you can learn a great deal from your first attempt and you could certainly keep trying until you perfect the process over several seasons.
As far as making pipe tobacco AND cigars, that's two different sets of skills altogether and I'd say you are probably better off perfecting one or the other unless you know any jack of all trades tobacco growers/processors to have at your beck and call!
PS: Shawn, that sounds really cool! I've wanted to make my own molasses-cased pipe tobacco but I've never thought to take it all the way from the leaf... Good luck.