You tend to be far more forgiving when something is both free (beer) and, feels like it belongs to you instead of some distant oligarchy.
Only if what your doing is of little to no value. The Windows tax is trivial compared to what I use my Windows machines for. The genuine advantage thing used to bother me, but then I grew up and just realized that I got so much use out of the OS that the price wasn't really that bad. I'd spend more in 2 days getting drunk off my ass on the weekend when I lived in Orlando than the cost of Windows XP Pro, which I've used for everyday for the past 9 years, on most days for more than 8 hours a day.
The genuine advantage thing has only been a problem for me once, on a work PC, where the previous guy had used a stolen volume license ISO to make an image. The volume license was revoked, GA bitched about it, and I had to enter the key on the side of the machine and give MS a call. The only people this really bothers are pirates (which of course it doesn't bother much) and others who did something they shouldn't. Its really not that big of a deal and MS isn't the first to do it, its just a battle cry for those that don't have a real battle cry.
Free (as in no $$$) doesn't make me any less pissed off when it breaks. Being free doesn't do me any good when the time that it breaks is near a deadline that I'm struggling to meet in the first place, or when it breaks and I have to go to the data center with 3 hours of sleep after a long day. I am JUST as pissed off at the 'Free' software and OS as I am at the one I pay for.
You may not care, but my time is worth money and when you realize the cost of the Windows tax counts for a few hours of my time if I'm buying a new copy of Win7 ultimate, no upgrade
I still use the free software as my BSD web servers have uptimes going on 3 years now and I'd never get that out of Windows, but it has nothing to do with the cost of the software and everything to do with how much time I waste dealing with 'issues' with that platform.
Multics is security spelled sideways.