Scott -
I spent a couple of weeks living in Pinehurst right around the New Year this past winter. I have spent a considerable amount of time in the area over the years.
There is no doubt that Pinehurst is the big dog in town but it's also very, very "corporate". If you've never been, I would absolutely play #2. If you must play another course on the property I would add a round at #3 or the Cradle. #4 is just fine and to be honest I wouldn't waste your $$ there when you could drive down the road and play Mid Pines, Pine Needles, etc.
The Cradle is very fun and I would take some time to hang and play there. At ~$75 make sure you have enough time to at least play it twice.
After #2, I would spend your time playing Mid Pines, Pine Needles, Southern Pines, etc. More affordable but also much more interesting than pretty much anything you'll see at the Resort.
Tobacco Road is a must.
Dormie is really good but don't sleep on a day at Forest Creek playing the North (!!) and South courses there. Very good.
Downtown Pinehurst is fun. Drum & Quill was my favorite pub in Pinehurst, followed by Duggan's.
I think downtown Southern Pines is probably more charming than Pinehurst and has a number of great local spots to eat & drink. The Sly Fox is a great spot.
Have fun - don't forget to spend some time walking around both downtowns checking out all the antique and book stores. Very fun!!