Risks of paying a Freelancer in the Iraq / Kurdistan Region

Via a website, I've found a programmer living in Iraq / Kurdistan. He's very good (provably so) and I need him to implement a couple of features in one of my websites.

My fear / concern is that if and when I pay this person for the work (perhaps via PayPal or BitCoin), I'll trigger some flag in some database somewhere, and if any of that money ever ends up in the hands of some enemies of the U.S., then I'll be in big trouble (suspected of providing material support to enemies or worse).

The situation is further complicated by the fact that I'm a permanent resident of the U.S. and intend to apply for citizenship next year.

Got any advice? I'll be monitoring this thread and responding to your need for clarifications.