Anyone watch 'Sex Change Hospital'?
The surgeon is transgender herself, she is still a qualified OB/GYN, and she discusses some of the difficulties with female to male changes.
She admitted she doesn't like doing vaginectomies because they're very, very bloody with a lot of potential to go wrong.
She did a hysterectomy once, however, and it took all her skill to be able to do it vaginally. For one, the person had never had children before, making it harder to remove the uterus and other organs vaginally, but an even bigger factor was the effect the male hormones had on the anatomy.