NIght 1: - I would take a 5-minute cab to Gene's in Manual Reef Marina. The food is Caribbean home cooking and is run by Gene and her husband, Robin. You really can't go wrong! I do enjoy the beach bar at Nanny Cay for lunch but have never been impressed with the night options.
Night 2 - stop by Willy T during the day and see if they have fresh fish for dinner service. If they do, you can't go wrong. Surprisingly, the food is really good at Willy T even most people associate it with drinking.
Night 3&4 - I love Hendo's and would never discourage you. Personally, I've never had dinner there but I'm sure it's good. I'd save it for lunch and try something different for dinner. Tipsy Shark is a great option. While you are on JVD, don't miss the patties from Sugar & Spice shack by the ferry dock. Joan is truly a gem but don't forget to say good morning/afternoon when you walk into her store.
Night 5&6 - as you say, everyone has their favorites. My go-to dinner places are now Sid's (best place to have a drink with local friends) and Wonky Dog. I like Anegada Beach Club, Big Bamboo, Cow Wreck, or Tipsy for lunch.
Night 7 - If your schedule changes and you aren't there for the BBQ night, get a cab and go to Coco Maya.
Night 8&9 - I'd definitely skip Saba or maybe stop for a drink during the day. I think BEYC, Oil Nut, or North Sound Bistro (this would be my 1st choice) are going to be better options

Oil Nut has a very clearly marked channel that starts between Saba and BEYC. Hard to miss, really...

Sounds great and it's making me hungry! Have fun....