@cksk2016 I was in exactly this same position last October except in Mexico. We renewed our vows and had a super miniature size group, which ended up only being 4 of us. We had our ceremony off site then had a beautiful dinner in a really nice restaurant in Playa del Carmen. I had the same thing happen. I had our photographer booked and wanted him to do getting ready shots and a first look at the resort where we were staying. Plus I booked the makeup people to come and do my hair and makeup and my friend's hair and makeup so that we could get ready at the resort. Wrong! They only charged me $105 which is a day pass for the makeup people but the photographer charge ended up being $435 and it didn't matter how much we argued they were NOT getting on board. I had the same argument - we weren't using ANY of the resort facilities or vendors. We were leaving the resort. They didn't listen to any of it. They said we had to take a 2 hour package with their photographer which was going to cost $350 no matter what. I knew nothing about them, about their quality. I don't even remember the name right now. I told my husband that it didn't make sense for a photographer that we had already paid a fee to for a 5 hour package to not come to the resort and pay another $350 for someone I knew nothing about. I stood in the resort lobby and cried. To me it was just so unfair. My husband is so amazing. He stepped in and we paid the outside fee.
I really don't think you'll get around the outside fee for your photographer, but I would absolutely try and get the makeup people in for only a day pass instead. The one thing that works in Mexico (not sure with Jamaica) is that the top makeup people do airbrush makeup and the spas at the resorts don't so you can say you're getting a service that the resort doesn't provide. It doesn't always work but it's worth a shot.
I've been on this site since 2010 and the number of times I've heard from brides about the outside vendor fees they get charged..... if I had a nickel for reach time I'd be rich I think. It's one way resorts really do get you. Most of the vendors they use aren't really much good, especially the photographers. I've heard of brides here paying $800 and $1000 per vendor in fees, mostly for photographers, which really is outrageous. For us, in the end, we used the resort's gardens and little bridges for pictures. Since we paid the fee I made absolutely sure we went anywhere we wanted to for photos.
I'm absolutely certain you won't regret going off site. I'm soooooo happy we did. Places I looked at just didn't cater to really small groups. Wanting to stick us in a la carte restaurants with all of the other people around just wasn't on my radar. We got a great private room in a restaurant that closed us off form the rest of the venue and it was absolutely great!
The other thing to look into is whether or not your makeup people have an off site salon or somewhere that you can go to for having your hair and makeup done. I looked into it and if I had known ahead of time it would be an issue I would have picked a resort closer to town because it absolutely was doable. But it would have meant more than an hour's travel and we were already tight on time. That may be worth it for you if they're able to do it.
Good luck! it's a crummy thing that the resorts do and sometimes you need to be creative to make it work but if you can figure it out it will all be worth it.