We ended up making a decision and now going to Hawaii much earlier than expected, after discussing it further, a 10-day trip just works a lot better for our schedules than a 2 or 3 week trip, so we decided to just pick one island and settled on Oahu as we really want to go to both Ko Olina and Aulani. Then we decided to deposit the whole 2 bedroom to ensure that we would get a 2 bedroom, but also allow us to shoot for a 3 bedroom, grandparents would be coming so would give them, us, and the kids each a room.
Originally were planning to go to Grande Ocean this October, but it has been a challenge figuring out the best way to get there from Toronto, we had decided that driving to Detroit and flying from there was our best option and we were about to book when we saw the Ko Olina drop including a 3 bedroom this Fall, we quickly checked the flights and they were surprisingly affordable with a manageable connection in Vancouver, total of about 13-14 hours each way. So we just went ahead and took the 3 bedroom and are now going the last week of October, Sunday to Sunday at Ko Olina, we fly in Saturday and plan to stay at the Best Western by the airport the first night, then Aulani on Sunday and Monday before getting back Tuesday.