I went to a hipster barber Wendy. The thinking being I wouldn't get any 'pity face' (I didn't). They gave me the biggest gin and tonic I've ever had to sip while it was happening and comped the entire thing! So kind.
I also found the spots where it hurt was where the hair came out. It was really weird when most of it had come out, and when I'd been barbered down to virtually nothing, I'd have these odd patches of painful stubble. They came away in the end. Mostly rubbed off on the pillow.
You do what feels right for you. There's a freedom in being bald. I quite enjoyed it. Wouldn't choose it but as a life experience, not the worst one I've had! K xox