I've done it a few times, with different parties. Never had any problems but yes there must be some level of trust. Good advice to exchange copies of DNI/passport, and to do a small test amount first. Of course one must always check the locally-exchanged Benjamin Franklins on the spot, this is just common sense. Always keep it below US$10K to avoid the obligatory U.S. IRS/TreasuryDept. notification.
Technically, easiest way for me, (far easier than a wire or ACH transfer), is if you both can open a Schwab Investor's Checking account. Then all it takes is a Skype or magicjack phone call and the stateside transfer is done instantaneously and without fees, simultaneously with the cash handover here in BsAs. Optionally you can conference-in both parties on the phone with Schwab. Also for me, for small amounts <US$10K, this method is easier than Contado Con Liqui, and the recent blue rates yield results comparable to recent CCL rates after commissions.
- Jim