Thanks for all the help! I got the trip booked for early 2021. Based on the recommendations here we went with a 3 island Hawaii plan: First 3 days at Hilton Hawaiian Village Waikiki Beach Resort Rainbow tower oceanfront, no car rental here. Then fly to Kauai and pick up a convertible rent-a-car, and spend 5 nights at Waipouli Beach Resort and Spa Kauai by Outrigger at Kapaa/Wailua. Then fly to Maui, get another convert, and stay 6 nights at the Royal Lahaina Resort Kaanapali - Beach, then fly home. THe travel agency picked everything for me, so I hope they did OK. I do have to kick in a big chunck of $ myself, as it exceeded the $5000 award. But still a good deal.

Now that I know where we will be, I need to hone in on an activity schedule for each island. Suggestions are very much appreciated!