I have thick hair, in my 20s I had it waist length and got it cut off in a short bob. Then I went to very short/pixie cut. Upkeep was weekly cuts/thins, but I didn't have to use product if I didn't want to. I lived with my hairdresser so cutting was free, so was product.

I'm in the process of growing my hair again, it is just shoulder length, don't know how much longer I'll grow it, I'm usually on 5 weekly haircuts but right now I've not had a cut in over 2 months and it is showing, I need to get to the hairdresser in the next couple of weeks.

I've never regretted cutting it each time I have.