To answer some of your questions: We didn't have a private reception because we only had 37 people. We just had the semi private dinner at Uncle Tony's. It was more like fully private because no one else was in there the entire time.
We used the resort's DJ and he was just meh. He's fine if you just give him your ipod and have your playlist ready. But if you don't, he doesn't have many songs available. I was told he would be able to download any song he didn't have so I didn't bother bringing my ipod. But after I talked to him, that wasn't the case. So, after about a half hour, my husband ran back to the room for the ipod. He didn't make any announcements or say anything at all. If I had to do it all over, I would either bring my entire playlist and ipod or use someone else.
The only outside vendors we used were Roan Robinson for our photographer and Rashel Edwards for makeup. Roan was great! He did arrive a little late but that wasn't his fault. The hotel was giving him problems with the whole vendor fee thing. But other than that, he was awesome! Rashel was amazzzzzing!!! I highly recommend her!!! She did my makeup and all 3 of my bridesmaid's makeup. She was super sweet and did a great job. The makeup lasted the entire day!
As for the timeline, the wedding was at 4:30, but didn't arrive there until about 5 since the photographer was late. The ceremony lasted about 20 minutes. After that was the champagne toast and picture time. At 5:30, all of the guests headed up to the Bob Marley Terrace for the cocktail hour. Dinner was from 7-8:30. The cake cutting was right after dinner at the Steakhouse. Then we went back to the Bob Marley Terrace for dancing from 8:30 until 10:30. And then some of us went to the disco. The whole day went sooo fast! It was everything I imagined though aside from the crappy DJ.
Hope I answered some of your questions