One main obstacle for their cloud business in general and specifically Azure is that the latest GDPR rulings in Europe basically says that it is illegal for European companies to use Azure (or AWS or GCP) if you store any personal information. This may be a hindrance for both MS and Amazon for the next 1-2 years.
Search for "schrems ii ruling" to read more about this.
I am not sure if you are claiming that MS is bureaucratic inside or the tools and applications they create are hard to use.
If we are talking about the inside then it does not seem to have stopped them from becoming gigantic.
If you mean that their tools and products are hard to use then I think it differs a lot between products. VSCode is for example very easy to start and use. GitHub seems to get better all the time and is also easy compared to other similar tools and so on. You could say that things like Office is hard but I think they are easy to start using. The hard part is learning all/many of the advanced features and that is ok IMHO.
As a parent to teenagers I can say that they seem to be able to sit still in front of a computer for _hours_ as long as it is a game or a tv-show they like.
(I agree that it was a bit optimistic to expect this of 5 year olds)