I was the one who kitted up the first serving man transitioning to a woman in the Canadian Forces in Ottawa in 1998 (or 99, I can't remember exactly). I do remember one of the major issues at the time was funding for the change in uniform from male to female because they had already received their entitlement to the uniform years earlier. I'm pretty sure they just absorbed the cost as well as the cost for the surgery, $40k plus at the time.