I wouldn't bother with sending the booze. For the cigars, make sure he's got a way to store them or else they'll get way too dry. If he's got access to a humidor (we had a few in our office in A-stan), then send the sticks along with some Xicar humidor fluid. If not, then make sure he's got a humidor to store his cigars as well. I've gotten reliable ones for $30 so they don't have to be fancy.
As an aside, I made some of my best friends sitting around firepits in Afghanistan smoking cigars, especially around the firepit at FOB Ghazni. Three of us got together last night in DC for booze, Padrons, and a good meal. Cigars are worth their weight in gold in a place like A-stan because it gives you a chance to process everything that's going on with people that are enduring the same stuff.