To throw .02BTC in this sounds dangerously familiar to Hawala networks which are becoming illegal in many countries after 9/11. The only difference is you are pre-negotiating the settlement of debt with Bitcoins.
Yes, very similar to hawala, although hawala probably serves the function better currently because of the pre-established trust. Existing without paper and/or transaction records for nearly 2000 years, hawala is nearly impossible to prove. Bitcoin solves the clearing function of hawala but not the settlement-into-local-currencies function. Therefore, any bitcoin exchanger/point-of-transfer in a country that is not on the FATF/OECD blacklist will have to comply with AML and KYC guidleines.