Hey! I did end up using John Wheatley as my DJ and steel drum band for my wedding in Jamaica last April. I would recommend using him for the steel drum band but not as a DJ. The steel drum band was great - they sounded wonderful. I had them play for about 30 minutes before I walked out, they played "here comes the bride" as I walked down the aisle and then for about 30 minutes afterwards. An hour and a half was about $400. The guests loved it!
After that, the band left and John Wheatley was the "DJ." I had emailed him and talked to him on the phone several times before the wedding to make sure he had the music that I wanted and that I could hook up my iPOD to his equipment just in case. He assured me that he had tons of music and all the songs I specifically requested. Unfortunately, all he had was about 10 CD's that I had never heard of. He didn't even have any Bob Marley. I then asked him if I could hook up my iPOD and he said his equipment could not accomodate that because he didnt have the right cable (the one that hooks to the speakers). I was definitely not happy! Fortuantely, one of my guests had the iPOD cable in his room at the hotel and took a cab back to get it for me. If it weren't for my guest, there would have been several hours of horrible music!
That is the one and only thing that went wrong at my wedding. The ceremony on the beach was beautiful and all my other wedding plans, arrangements, vendors, etc. turned out wonderful. Hope that helps!