Hey Scott,
I've been in the Cigar.com cigar of the month club for quite a while and have been pleased with every package. The main benefit is that I get to try many cigars that are new to me and some that are hard to find. If you're just getting into cigars it's a great way to try different cigars and find some you really like. The value of the cigars themselves has exceeded the monthly cost of the club every month that I can remember.
Hope that helps some,
Dean