I know when I quit smoking cigarettes I'm glad I wasn't into cigars. I probably would have just transferred my nicotine addiction. As it is, my cigar addiction leans more towards the collecting, herfing, gifting, and comraderie than the actual act of smoking (don't get me wrong, I like that part too!)
My suggestion would be to follow nhcigarfan's advice and quit it all cold turkey. Give yourself a month. Then take your average of 2 cigars a day 5 days per week, lowball the price (say $4 per)...after a month, you've saved $160. Take it and go buy a nice box. Hopefully you won't have the craving issues and you can enjoy a cigar without having to have one.
Good luck in whatever you do, Shelby. I'll be pulling for you.