Sadly, for male to female (M2F) hormones do very little to the voice. All the work has to be done in one's throat and head. You raise your voice into your head and take it out of the chest. For Female to Male (F2M) then the hormones do drop the voice, just as testosterone does to pubertal boys who were soprano.
All the work you can do with your voice to raise it (not falsetto as the stereotyped male to fe,ales are shown on television) takes considerable skill. In my case chronic sinuses have severely limited me, but very acceptable 'feminine voice characteristics' are achieved when medically able. Trying to sing, while sustaining that, is very hard and I suspect that is why the person you speak of Richard has a non convetional delivery. That said, many women I know have very low voices and some men quite high ones. They enter into a very androgenous area. As long as the voice is pleasing then it matters not to me. I envy those who can thus move their voices when singing too. I am never jealous though. I am pleased they are able to get where they want to be. It all adds to overall richness of sounds and some songs need very different deliveries.
Sometimes it can be really hard work being me and I am sure it is hard for others. With more acceptance and encouragement though, support and enthusiasm, it does get a lot easier. But that goes for singing generally don't you think? We all need the gentle prods and guiding. We all need the smiles and the encouragement. We need to know our songs are reaching out. One of the biggest thrills of singing publically is to be able to share. Not having an audience/like minded folk around would make it so less meaningful. It's also nice to listen too. We all have our hopes and aspirations, our dreams and ambitions. Some are lucky to get a good shot at them. Some manage to achieve them.
If my life has taught me anything it is: Never give up hope
To quote a well known song
"Fairy tales can come true, it can happen to you"