For Hilton Hawaiin Village - Oahu
Since you want a 2 BR HHV - Kalia tower is out as they only have studios and 1 BRs. HHV - Lagoon Tower. If you can afford a Premium (Oceanfront) unit then get it, otherwise, opt for the PLUS. Waikikian is going to be nearly double the points for either the Lagoon or Kalia towers, so if you have the points there will likely be availability. But opt for Lagoon Tower if you are trying to use mimimum number of points.
If you are interested in the Big Island you have several choices as all resorts have 2 BR units. Again plus or premium will give you better views or locations/size. Bay Club will be likely the easiest to get in, they offer 2 BR and 2 BR+ only. Waikaloa Beach Club offers only 2 BRs units, in standard, Plus and Premium. Kings' Land, like the Waikikian, is in a new higher points chart scenario, and offer only plus and Premium in the 2 BR. Take Kings Land only if you have points to burn.
Mark your calendar for 9 months out, to ensure you get your unit, book the first 3 days using an online changable reservation. Then for no extra charge you can keep adding each additional day as it becomes available in the 9 month window.