Being prepared "95%" is a pretty high bar, not a lower one. Personally, Id say many are lucky if they break 40-50%.
I think whats at play here is, you have groups of people who have different ideas as to what all this is. Some think having a gun, any gun, is all you need, some understand that theres more to it than that, but they really dont want to invest any more than they think necessary into it, and then you have those who understand that if you want the best chance at things, you need to invest time and effort into it if you want to be towards that 95% level.
Experience and having run the gamut so to speak, also has a big input as to understanding things. When you hear that its not possible to carry pretty much anything you want, year round, and in your normal street clothes, you have to wonder what that persons actual experiences are in doing so, or not, especially when youve done it your whole life, and never really had any issue doing so.
This isnt about can or cant, its about "want". If you "want" to do something, you pretty much always figure out a way to do it. If you dont want to, then you usually figure out a way to get out of it too. The latter is also usually the easier path too, as the former requires work on your part. I think thats whats going on here much more than the "its not possible" thing.
My base rule here for me, has always been, choose a gun you are very comfortable and experienced with, shoot well, if not the best with, and shoot it regularly in as realistic practice as you possibly can, and then figure out a way to carry it. Its not hard, you just have to want to do it. Once you figure that out, youll be well on your way towards that 95% goal.