I'm a wedding DJ with over 6 years of experience (98 weddings) in Costa Rica. I know that most weddings go for at least $1000 for decent 4-hour service in North America, but I charge about 60% of that for the same or better quality of service here. Because of the small population and the high price of imported electronics here, it is very difficult to find a DJ with experience, good equipment and attention to detail; logic dictates that good wedding DJ service should be more here in CR than up north!
Here are some of the most important things you are missing with the iPod wedding, especially in Costa Rica:
1. To rent the same concert-quality sound system equipment that I use here in Costa Rica is going to cost the same or even more as my service, and you will have to bring the equipment from and back to San José. 2. If you play through the house systems of most reception areas (i.e. crusty bar speakers exposed to ocean air or rain), it's just not going to have the same impact as a real sound system.
3. If you've ever attended an iPod wedding, you will be familiar with constant abrupt music changes and inappropriate music coming on at the wrong time. Of course there's also the drunken struggles for control of the iPod that often happens as the night wears on. Be prepared for lots of dead air and false starts as you try to search for that song that you can't find easily in the menus or remember the name of, that rap song with the N-word comes on during dinner, or the same song keeps coming on again and again.
4. Whoever is in charge of the iPod will need to maintain concentration over the entire night instead of enjoying the party fully. Most people unaccustomed to DJing end up failing at this task.
5. A pre-mixed set sounds like a good idea at first, but it lacks the foresight of not being able to change the direction of the music, especially if your group starts losing interest or someone wants to make a request.
6. A good DJ will help you plan an optimized playlist of the best music (and a "no play" list if desired) for your group ahead of time, and also be ready to take popular music requests from you or your guests at the reception.
7. A good DJ will be able to watch the floor and play music in a flow and appropriate volume that keeps you and your group dancing, as well as to connect with the crowd and direct the attention of your group enough to have a great time together.
8. A good DJ is also a master of ceremonies that can handle all of the special programming perfectly, including cocktails/dinner music, your introduction, first dance, parent dances, cake cutting, bouquet/garter toss, group games and activities, and even your ceremony music and vocal amplification needs if desired. You just can't get that from an iPod.
Hope that helps!
Joshua