First I think we need to separate those who have or who intend on transitioning from those who don't. Obviously if a person is a transitioning TS, then there is no choice BUT to tell … it's difficult to always leave the house dressed in the target gender, change a name legally, change all the gender markers, and through HRT grow breasts, soften skin, redistribute fat, plus work on changing the voice to match the gender presentation without people in the TS's life noticing. It's nice to receive responses from a TS's perspective in this thread, but they are under different circumstances than non-TSs.
Likewise, even though this represents a much smaller percentage of people, a person who identifies as pangender or other non-binary gender (agender, androgynous) and who lives and presents as such daily without switching back and forth, also falls outside the scope of this discussion since again, they have made the choice to live as they do 100% of the time. The choice to tell or not to tell is moot.
Getting back to your post, I do believe that your blog article applies to the people who identify male or predominately male (or somewhere in between male and female i.e. feeling they have characteristics of both) and who do switch back and forth, since doing this involves some choice, namely, the choice of when to dress and not to dress.
All this to say that I totally agree with the following statement from your blog as the primary reason to be out to loved ones:
"The question I ask is why do we feel this need? I can only speak personally here. On one level I think it would make my life much easier. If I was not afraid of a family member seeing my wife and I walking through a shopping centre I am sure I would feel less anxiety and thus have even more fun when doing so. Also, if my children (for example), knew about this other side of me, I could get dressed more easily and finding the time to be me would involve less logistics and less cloak and dagger activities."
Why is there a need for honesty? Because it makes life easier when people who are close to you know since you can live in harmony with them without having to resort to subterfuge … provided they accept. If a CDer chooses to tell a spouse, child, friend, or coworker who then says, "That's nice but I would prefer to not go out and do things with you dressed, or even see you dressed", then I wonder if there would be the same amount of stress involved in meeting this person accidentally while dressed than if they didn't know.
Living life authentically means the ability to present as you wish, when you wish, which is pretty much the decision that TSs make. They do not wish to constrain themselves to presenting male, ever. If after you tell a loved one or a friend, they still do not want to see you dressed, or they are OK with seeing you dressed at home but they don't want to do the things you want to do while dressed like going out, then you still are constrained to not dressing when you are out with them. It's better than being completely closeted, but there are still constraints.
You also mention going out in public and dealing with SAs, restaurant personnel, etc in girl-mode. This is much easier since the crossdressing doesn't impact any of these people's lives and so they just don't care. Additionally, they provide a service in exchange for money, and if they want your business they need to not have (or not show) a personal opinion of your presentation. Would these same SAs, restaurant personnel, etc be as accepting if their husbands or boyfriends were CDers? It would be interesting to ask them.
As to neighbors, I think they fall into an in-between category unless they are also close friends with whom you do things with socially. If a CDer lives in a neighborhood where they don't know their neighbors or they are strictly casual acquaintances, then they also fall into the category of people who are not impacted by what you do ... although it might be more complicated if the neighbors also know your workmates, close friends, or other people whom you do not wish to tell in which case there would be a risk of gossip.