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Dear Gardner,
You need to do what is most fun for you, but if the idea of salon sets makes you anxious, but you are interested, get over it. Most people could not care less.
The first time I let me hair grow out I got through the difficult stage only by having it set at least twice a week. That way it did not go wild. Then when I was able to tie it back, I only got a set for formal occasions when I wanted it to look especially full and neat.
Last year I took a major trip that involved tramping over lots of archeological and historical sites, and I thought it would be easier with short hair so I has it cut to about 5" and got a curly perm. That was fun to, but as it began to grow out it was more difficult to manage than the long hair, so as we speak my hair is about 1" short of the length needed to pull back from my temples and tie it behind, so I would say it is about 8" I am getting it set every Monday and Wednesday, and if I have any important even at work again on Friday. It takes some time, but it is rest time and I read the newspapers.
I have three different salons I go to. The one in my neighborhood is a FantastikSams and they do not take appointments. I know when it is best to go and there is one woman who does a great job for me. Two others are nearer my office. One is run by a very bright woman eager to learn and we have good talks. The other is run by a very skilled by amazingly dumm man who makes me silently moan when he shares his wisdom. But he does a great job.
By September I should be able to revert to a set schedule that is based on when I want to make a specific presentation -- otherwise I wash it, let it dry or tie it before it dries, comb it once after it dries and it looks very presentable.
James