Just diving into this conversation......I've been to HHI every month of the year over the last 25 years. It's really great all year, but different. My least favorite time of the year to go is summer time due to the crowds and heat, but I've done that a dozen times and had a lot of fun. During non-beach season it isn't very busy and getting into restaurants is not a big problem, so keep that in mind. Given what you want to do, I would go with Grande Ocean followed by Monarch, Harbor Club in Harbortown, Surfwatch (you will get gardenview as a trader), Barony (great if you were to get ocean side/front), and then the ones at Shelter Cove. Heritage Club is also good (in Harbortown), but it doesn't come up in II very often.
Don't worry as much about the specific location of the resorts in terms of where they are on the Island. Everything is no more then 20 minutes away no matter where you stay. Grande Ocean, Monarch, Heritage and Harbor all come with Seapines passes which saves $9(?) per entrance if you stay at another resort and are walking/biking distance to lots of restaurants. The ones at Shelter Cove are too, but it's a big trade back in terms of the units themselves. I would definitely explore the Shelter Cove area since there are some very good restaurants there, a huge Kroger, and a Whole Foods.