I have no problem with a man becoming a woman or a woman becoming a man. It has literally NO effect on me, and therefore I cannot object to it. I do find it strange, and it is certainly something I would never do, but I support the choices that people make and feel they should be free to do as they please.
Richard Simmons is a grown adult of sound mind. He has the right to change his gender from man to woman if this is what makes him comfortable. All adults should have the right to change their gender if they want to. Just because someone is born a male, it doesn't mean they will always identify with being a male. Likewise, someone born female may actually identify with being male. In short, people should have the right to live happy lives any way they can that doesn't harm others.
I remind myself of one rule everyday; I live my life, they live theirs. I understand the hesitation towards the subject, but unless you feel the way a trans person does, you can't completely judge their situation. I myself have always felt female in a female body. I couldn't imagine feeling any way else. It would seem like torture during the one life that I have.
There's increasing awareness of and reporting on transgender issues in the media today, but there is also still a long way to go towards widespread understanding and acceptance. Gender confirmation surgery, for those who choose it, should be available and covered by insurance. And discussions of celebrities is fine, but it's also important to remember the issues facing most transgender people, in terms of employment and housing discrimination, poverty, and other things.