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I've heard great things about this resort
Hawks Cay anybody else?

Sounds like you are narrowing it down. Here is another option for affortable and reputible villas http://www.wyndham-vacations.com/main.t ... de=846460A

If you are looking for high end villas I can share some resources there too, just pm.

OKC great place. OKC memorial is best viewed at night. In Bricktown Mickey Mantle's Steakhouse/ bar is great, also enjoyed Toby Keith's place.There is also a great little BBQ place on the edge of town...can't remember the name though.

Is this something you are looking to do annually? with the kids too? Same destination each year?

Broadmoor, Antlers Hilton, Marriott quality accomodations with banquet possibilities. Can be of more help in this area if needed.
Olympic Training Center, AFA, Pro Rodeo Hall of Fame, Garden of the Gods Park, etc.

How long are you looking to stay...a week?

Been to Cancun, Cozumel, Jamaica (Negril&OR).
Favorite was Negril, Jamaica.