Perhaps they are dealing with a public perception that they are 'old sauce' which is to say "Oh my grandparents used Windows, I use <something else>." Technology has its fashion moments and this is one of them. When you elevate the OS to the level of 'brand' you enter into a world where fashion as well as features dictate acceptance. So in that world, they need to have a fashion statement as well as a technology statement.
That being said, its also easy to get stuck in a rut and have that kill your project. Microsoft has perhaps more scars than many in this area. If you recall they did a 'tablet' version of Windows long before iOS, but they failed to 're-imagine' and instead they tried to 'shoehorn' ideas which didn't make sense (we'll assume you have a high precision pointing device like a stylus or mouse) and so those preconceptions prevented them from seeing what needed to be done.
Mostly I think the messaging about the flag and what not is PR to try to tell people "Hey, we're awake and we're trying to innovate, and we want to be better, and we're sorry for Vista." If their stock price is any indication they are having some success there.
Well in XP Tablet Edition, people with touch screens did have a high precision pointing device. Capacitive screens were uncommon with end users at that time, and almost unheard of (completely unheard of?) in laptops. I don't know if Vista had a tablet edition, but in Windows 7 it's pretty easy to get around the basic OS with a finger. The only real difficulty comes in with third party apps that do not follow finger-friendly design concepts.
Even for Windows 7 checkboxes, I've seen capacitive screen drivers/software that allow for some "fuzzing", where if you hit somewhere around the checkbox/button, it gets checked.
That being said, its also easy to get stuck in a rut and have that kill your project. Microsoft has perhaps more scars than many in this area. If you recall they did a 'tablet' version of Windows long before iOS, but they failed to 're-imagine' and instead they tried to 'shoehorn' ideas which didn't make sense (we'll assume you have a high precision pointing device like a stylus or mouse) and so those preconceptions prevented them from seeing what needed to be done.
Mostly I think the messaging about the flag and what not is PR to try to tell people "Hey, we're awake and we're trying to innovate, and we want to be better, and we're sorry for Vista." If their stock price is any indication they are having some success there.