I wouldn't be worry about bringing your photographer to the resort - as soon he is not Cuban. Law in Cuba allow to charge only 200 CUC for a wedding service and there is no way that Cuban photographer will be able to survive , buy equipment (which is very expensive - we travel with $20 000 in our bags. This of course sucks and I hope that this will change one day. Only thing we can do - as photographers - promote weddings in Cuba, bring staff for people when we are down there and educate local photographers. Every time we bring laptops, used cameras, DVDs and leave there.
As soon your photographer is Canadian, European (etc) he is a tourist in Cuba. You don't hire photographer in Cuba, he doesn't operate a business there. He is there as your Canadian guest. Yes, you have to pay a day pass to the resort and they will treat your photographer like your guest. What's goes on in Canada that's not their problem.
You don't pay in Cuba for any services. Nice tip for your wedding coordinator (like perfumes from Winners or whatever, doesn't have to be expensive) will help for sure.
Please PM if you have any questions regarding specific resorts.