It's all about the 'apps' Luke
Not the OS.
I migrated our small business to Linux at the start of this year, and it was the best thing I ever did quite frankly. None of the users are 'young' and I expected a degree of resistance from dyed in the wool MS users. The reality ? Barely had a problem with Linux. Much less than I ever had with Windows (and we were on XP).
The trick was the apps. I got them to use programs that would be the same on both systems for a while before the change - Firefox/Thunderbird/LibreOffice etc
The ONLY program that we couldn't change was Sage, so we dumped it - the reality was (in hindsight) that one program alone cost us a fortune in time and energy, and money. It really was awful, along with the support. I just felt like an udder being constantly milked. I guess we could have VM'd it - but dumping it was way more satisfying. The best chat with Sage I ever had :-)
Admittedly the big companies have the luxury of leaning on their suppliers for change which small ones don't. But there is an answer for most things if you throw away your prejudices and take a little time to look. And if it doesn't break, you don't need much support.......
Hardware has not been a problem as we were using slightly older machines. Just check everything before you go - fail to prepare, prepare to fail. Anything suspect (very little) was dumped for something that worked.
Desktop Linux has come a long way. it still isn't perfect, but then what is ? Maybe with more users, there would be more pressure to resolve some things which are still annoying. However, I spend far less time sorting out OS issues, and more time on actual work.
Ironically, just recently it took me an hour to find and fix something on a friends Windows 8 system which would have taken me 5 minutes in XP, purely because I couldn't find what I needed when I needed it. I found the learning curve is much bigger than it was going to Linux.
I also just ran a test on a friends laptop. An typically 'underpowed' Windows 7 spec, it took 2m 50 secs to boot to a desktop with Firefox and Skype open and on the ragged edge of swapping itself to death. Xubuntu took 50 seconds to do the same with plenty to spare. I was gobsmacked to be honest. I've recently been converting a lot of older XP machines, used in the main by older than average users (a lot of pensioners). My phone has not been burning with support queries.
The reality is that Linux ISN'T that hard either to learn, or maintain. Certainly no harder than 'learning' Windows, and is not something to be scared of. It has its pros and cons like any system. I just feel a lot of the MS people here put Linux down without really having tried it properly. Maybe it isn't for you. But at least now you have to upgrade from XP, forget the scaremongering and give it a decent trial.
And for the record, I was a long time believer in MS. I just woke up one day and smelled some coffee :-)