If I had to plan a trip to Pinehurst and money and access were not in the picture, I'd play #2, #8, Pine Needles, Forest Creek (Both), and CCNC (Dogwood) before I played any others. After that, I'd take the drive to Tobacco Road and play Southern Pines. If you can't get on the private clubs, I'd play #4, Mid South, and maybe the Magnolia at Pinewild. If you want the long drive, maybe go to Tot Hill Farm.
I have never been a big fan of Mid Pines, not that its bad, I just didn't think it was that good, to me, its the least good of the Ross courses in Southern Pines/Pinehurst.
Beyond the ones I mentioned above, the rest are essentially point and pick, there's not really a dime's worth of difference between any of them.
As for the Pinecrest, I've said it before, I was less than impressed with the food I got. But its a cool, cozy place, certainly cheaper than the Holly or especially the Carolina Inn at the resort. The Lodges at Mid South are pretty posh and right on the course at Mid South; the Villas at Talamore are pretty good as well, though I would only stay there and not bother playing Talamore. I've heard the Lodges at Pine Needles and the Mid Pines Hotel are very good as well. The rest of the hotels in the area are pretty much coin flips, they're all about the same.
PM me if you want more info about specific courses, I've played pretty much all of them in Pinehurst that are worth visiting on a trip.