FWIW I always got (IMHO) good haircuts from Reed's on Trumpington St (near Brown's IIRC) for around a tenner, so if irritation with barbers is a concern then I'd try them. I may just have low standards, though.

IIRC Dawn has some software from Cosmopolitan or something for virtual makeovers. It may not work as well for giving males very short hair, but it might have the additional benefit of helping you choose eyeshadow. (-:

If it's any help, my scalp skin seems to be in better condition that I thought it was, so that worry about hair shortening proved to be needless.

If it all goes horribly wrong, pretend to be your brother for a couple of months who's helping you out after a temporarily-debilitating accident. (-: