Michael,
Congrats on your eventual move to Pinehurst. I thought about moving to Pinehurst myself, and did some research. I found that Pinehurst Resort is great, but the resort comes before the memberships - as you noted some reasons already. I also looked into Mid Pines and Pine Needles, now shocked to Jay talk about the tee sheets being filled already.
I do treasure being a member of a private club so I can go out when I want and practice when I want and get a tee time when I want.
Pinehurst move fell through 2 years ago when I brought my wife and kids. I was the only one that enjoyed the visit, so that place has been scratched off the list of places to retire. However, I will continue to visit my friends in Pinehurst and play some really good golf courses.