But that was 13 1/2 years ago. No wonder people are uneasy about Microsoft. Windows 7 is just a patched Vista - doesn't really fix the underlying problems. Windows 8 actually did - and is their best desktop OS ever - but UI schizophrenia scares people away. Yet even Windows 8 requires more maintenance than OS X - in spite of the ever-increasing bugs in Apple OSes.
Nothing wrong with Windows 7 and the main UI issues in Windows 8 have been fixed in Windows 8.1. We're deploying 8.1 at work and users have no problems with it, most prefer it.
The Windows maintenance issue is blown out of proportion, I doubt OS X actually has less patches issue than Windows does. Microsoft tend to release a separate patch for each issue, whilst Apple tend to roll them up. Plus a lot of the Microsoft updates are for other products, rather than for Windows itself.
Not sure who you think are feeling uneasy about Microsoft, unless you're referring to senior management at Apple? Microsoft are on a roll, the new products and advancement they're putting out across the whole of their business is impressive to say the least.