I've only had him cut my hair once, as I just went CG about 5 weeks ago. He did chop off about 7-8 inches, as I have been straightening my hair (Japanese and keratin, along with hot dryers and irons - it's no wonder I still have any hair!) for many, many years and the worst damage was the long part, and that part was still mostly straight so it looked kind of stupid. I still have about 2-3 inches left to cut off but he didn't want to go any shorter the first time.
Good luck and let us know how it goes!
Not sure how often I'll go back - have to see how it starts to grow in.