I've had the luxury of playing golf in Pinehurst since 1990 (when the price was reasonable) and was even a member for 6 years. My take is that golf at the Pinehurst Resort is WAY overpriced, however you seem to want to play the courses so here is my opinion.
#1-Very short, but has some great holes and would be a good starter course.
#2-I guess you have to see it, but not worth half of what they charge for greens fees. It is an amazing course, but for the price, I would rather be looking at the Pacific Ocean on Pebble Beach.
#3-See #1
#4-It used to be an awesome golf course, but Fazio built a course that doesn't fit for the area. Not worth the money, but the new course is still a good test of golf.
#5-It used to be the hardest course at Pinehurst before they flatened all the areas around the greens and made the approaches architecturely uninteresting. The reason that it is so difficult is the amount of tee shots where OB comes in to play. My count is 11 of 14 holes (didn't count par 3's) have OB on the tee shot. I won't pay the money they want now to play this course again. Too bad, because it was a great test. It still has some Ross holes on the course, but it's mostly Maples.
#6-I think this is the best deal of the Pinehurst courses (unless they've recently added a surcharge). I haven't played it since they made some minor revisons, but overall it was a very enjoyable round of golf with the most elevation change of Pinehurst courses 1-6.
#7-My membership didn't include the course, so I've only played it about 4 times, but I liked it. Perhaps the most elevation change of the Pinehurst courses. They made some changes a few years ago and I haven't talked to anybody about the changes so I can't comment on the current course.
#8-Never played it as they wanted to charge members $180 when it opened in 1999. I don't recall hearing anything good about this course and I've heard firsthand from a few friends that it's not that great and way too expensive.
Now there are many other great courses in the area and some have been mentioned.
Pine Needles and Mid Pines are two of my favourite courses in Pinehurst so I would definitely play them and they should be cheaper than the Pinehurst courses.
Both courses at Pinewild are great. The Magnolia (Gene Hamm) and the Holly (Player) are fun, challenging, and also should be cheaper or the same price as Pinehurst.
I think the National (Nicklaus) is worth a visit, but I think it also quite expensive so there are other courses I would play.
The best values in the area are as follows:
Southern Pines CC-Easily the best value (perhaps in North America) and has some of the most interesting land that Ross had available in the area. About 5 years ago my Dad and I were in Pinehurst for 2 weeks and ended up playing Southern Pines 9 or 10 times (even though my Dad is a member at Pinehurst) because it is such a great course and an amazing deal. After noon with a cart (it's easily walkable) was $27. However in recent years the conditioning hasn't been the best, but the greens were always good. Go to the course first, to see what condition the course is in if you're worried. There should never be a problem getting on.
Foxfire (Hamm) has 36 holes and both courses are well worth the money. They usually have a great rate if you play both courses on the same day and even if you don't it's still a great deal.
Bayonet at Puppy Creek (Willard Byrd) if you don't mind driving 35 minutes east of town you won't be disappointed. It's a great layout and is always in great shape. It should be in the $40 range or less and I play it every time I go to Pinehurst.
Hyland Hills (Tom Jackson) if conditioning isn't a huge concern(it could be great or just okay) then I would suggest playing here as a warm up course. The layout is outstanding but there are a couple of greens that need reshaping because of slopes that are too severe (6th and 12th) but overall this course is the 2nd best deal in town. Should be about $25 with cart after 1pm, but again is easily walked and is the perfect starter course because if you don't play well, it's only $25!
Tobacco Road is a neat course, but can be the most frustrating course in the world depending on where the pins are that day. Some of the greens are dowright stupid, but if they're not charging more than $70 (they probably are depending on time of day) it is worth the look. It's also 30 mins north of Pinehurst.
The Pit (Dan Maples) is okay, but they are a handful of stupid greens and it not worth what they charge. I wouldn't pay more than $50.
I like Talamore (Rees Jones) but there are others I'd play first before paying the high green fee.
I could go on longer, but I won't. Here's my ranking if price is sort of an issue.
Pinehurst #2-You have to I guess
Pine Needles and Mid Pines-can't just play one
Pinewild-Both courses
Pinehurst #6
Southern Pines
Foxfire and/or Bayonet- depends on drive to Bayonet
Pinehurst #1-for historical purposes
Hyland Hills
If you don't care about price, sub in The National, Tobacco Road, and Forest Creek for Foxfire/Bayonet and Hyland Hills.
If you want any more clarification, contact me.
Sorry for the long reply, but I have strong feelings for the Pinehurst area and I think that Club Corp has ruined golf for Pinehurst.
thanks,
Evan