Can anyone recommend the best/cheapest way to send US dollars to Costa Rica? I'd like to avoid the Western Union high fees if possible. Thanks!

the best way to send money repeatedly to a trusted relative is ot make them a co-signor on a credit or debit card so they can get it out of an atm machine.

For a less trusted relationship visa buxx or simular cards that can draw from an atm might be better.

It really depends on the relationship, frequency and amount.

Definitely avoid any remittance houses that you see on the side of the road - these take huge commissions. Western Union is not terribly bad, but also takes a small cut (don't forget that VISA now will take a 1% extra cut on FX, so the ATM method also will cost you).

Depending on what internet access the recipient has, setting up an online exchange via Western Union of Paypal is not a bad idea. Just know that you are going to take a 2 - 4% hit for ATM foreign exchange transactions, a 3 - 5% hit for online FX such as Paypal. Honestly, there's really no way around these unless you want to start speculating on currencies.