Hi zetabyte,
I've updated all of my documentation to male, including my health insurance. I have heard of some guys having issues getting hysterectomies covered once they switch their insurance to male, but that has not been my experience. I'm not sure how much, if at all, it factors into it, but my insurance is a plan under the Affordable Care Act through Washington, DC where all sorts of trans exclusions are illegal.
I believe under the Affordable Care Act, gender coding is removed from procedures, so if a plan would cover the procedure for one person, they'd have to cover it for another provided the same medical necessity is present.