While I don't disagree, MS did have some issues making development of Windows harder than a ground-up development would have been. First, the notion of the internet didn't really exist, so the notion that things needed to be locked down wasn't even a notion. And of course, they had to maintain support for legacy hardware and software - the result of being the leader, but still a huge burden. Of course, what they put us through in those days would get them collective hanged by the eye-lids today. But I think people threat MS poorly compared to other OSes that didn't have the burdens that MS had to carry.
I have been using the Internet since 1986. MS was one of the companies that was on the original back bone in the 80s. Heck I remember editing our host list for them while I was still in the USAF because DNS wasn't even spun up 100% back then. Windows 1 was released in 85 and Windows 2 in '87. Both of them could have been written for the internet and weren't. In fact the single largest event that should have gotten MS' undivided attention, because they were affected by it, was the Morris Worm from '88 (was active duty at that time and watched it cause a huge panic at NORAD). So MS watched the computer industry grow and simply didn't care enough to learn from the very events it was living thru.
Their thought process back then was very clear. If everyone didn't have it, they didn't need to care about it. So back in the day when 150 and 300 baud modems were the norm and maybe 1 out of every 1000 PCs had one, they didn't want to care. That line of thought lasted until 2001. And by then it was to late because they had already designed Windows 2000's Ring 0, 1/2 and 3 so poorly that they didn't know how to fix it much less how to do it right even if they went back to the drawing board. BTW, they finally got a clue with Windows 7.
The burden you speak of was brought upon them by them because they never learned from the past or could even remotely predict the future. Just look at how long it took them to make Windows Phone 8 and Surface if you want any conclusive proof that they don't understand how to deal with the future much less react to the present.
And supporting legacy hardware would be easy if they wrote proper code. Linux distributions today still work on PCs built over a decade ago because they understand how to do it right.
BTW, Install Windows 8 over Windows XP and watch what happens to your installed Programs. Heck install Windows 8 over Windows Release Preview and watch what happens to your installed programs. MS has no clue how to do things properly based on those two facts alone.