LOL - yeah, I'd like to go all Linux myself, but there are some applications that I use on Windows that I've not found a good replacement for on Linux.
1. Adobe Audition - Audio editing (yes, there is Audacity, but it's not even close)
2. VBA in MS Office - I know you can run some, but with some of the items, I'm afraid to try and convert over. I know it can be re-built using Libre Office or other tools, but I don't really have time to learn the differences enough and also rebuild some tools from top to bottom to make them work.
3. Coupon printers - I've yet to find a workaround for them on any Linux distro - they all require windows (I realize there are some now also on Android / Google Play, but then my wife will have totally relearn some of the things she's done and I'd also need to spend some time helping her there.
4. Occasionally like to play games. I know there is better support there now, but there again - it takes a whole lot more work to get Windows games running on Linux than on Windows. Besides that, the games native to Linux that I've seen are just jokes.
So yes, it depends. If all you're doing is browsing the web, or maybe typing documents/letters/simple spreadsheets, then Linux might be okay. And even then, you have to make sure of hardware compatibility, etc. If you get the latest or near latest version of Windows, as long as your hardware isn't semi-ancient, then you generally don't have compatibility issues.
I have once setup a senior citizen on Linux, and she used OpenOffice instead of MS Office and Eudora (if I remember the name right) as a replacement for Outlook) several years ago. Well, she was doing really fine but ran into hardware issues on her printer (an HP printer at that). Just all of a sudden, Linux wanted to forget everything, and after I had spent hours and hours trying to resolve the crazy issue, I just gave up, and we took her back to Windows.
About 6 or 7 years ago, I tried - I really really tried - to setup a file server at my house using Linux. I was trying to setup a 2TB partition of 5 5TB hard drives using a hardware RAID card. Granted, this wasn't the best card, but at least it worked on Windows. I tried SEVERAL distros, asked questions online, researched, tested, etc, all to no avail. The issues were that either the system saw it as 1TB (losing half my storage) or it didn't see it at all. So I finally gave up that sinking ship as well. On Windows XP, it worked just fine, no fuss.
Bible Study software - the software I prefer to use runs on Windows, so it's using Wine on Linux or else going to a different program.
Basically, in my experience, if you have specific applications you use for specific tasks, then changing operating systems isn't so easy. If you just browse the web, or in general have simple tasks and do not really care about what programs you use, then conversion between OS isn't that difficult.
For me, it'd be like going from Windows to Apple. Yeah, some folks have loved it, but from the few folks I've helped on Apple machines, and what I've seen there, I'd rather just stick with Windows. I'd go Linux before Mac anyway. If I had to change, I'd suck it up, find SOME WAY to make things work, and just go for it.
With Windows 8.1 out, I have had the thought lingering in my mind again, but really... I can still use Windows 7 just fine. I guess eventually, M$ will stop supporting Windows 7 like other previous versions of Windows, at which point I'd have to go to something newer. I only hope that they come out with something better in Windows 9 or 10.
Yes, I did ramble quite a bit.
"But thanks be to God, which giveth us the victory through our Lord Jesus Christ." 1 Corinthians 15:57