I've run Ubuntu on a desktop machine for years and generally things have worked quite well. But I make sure that Linux will support it before I upgrade my video card.
I really prefer Linux but I wouldn't install it on a random laptop.
I do use Linux at work by way of Vagrant, and it's great for that. It's Linux on the desktop that appears to be unsuitable for everyday use.
You don't have that concern with Windows because mainstream PC manufacturers need to support Windows to be profitable, but there's the exact same problem with OS X. It feels a little different because the OS comes preinstalled, but you're still choosing the hardware for the OS.
If you buy a machine that is reputed to work well with linux, it works well with linux. If you don't bother to check that, you might end up with a bit of homework.
Never. In fact, my laptop connects to wireless networks even before I can unlock my screen.
But then again, I'm on a ThinkPad (with an Intel 7265 Wi-Fi card), and these things are well-designed hardware that try to stick to standards and are well supported on Linux.
1. significantly faster vioscsi(4) driver for VirtIO SCSI adapters -- I can live with vioscsi being up to 2x slower than Ubuntu or FreeBSD, but 5x - 10x slower is probably a deal breaker for some other folks that would like to use OpenBSD on Digital Ocean, Linode, etc.
2. binpatches directly from OpenBSD, similar to the way a third-party is providing them at https://stable.mtier.org/
Other than that, really love OpenBSD and even their man pages are awesome.
On the other hand, "cheapo refurb" is also indicative of my desire to minimize the expense of purchasing an additional computer.
I'm thinking of getting another just to have the parts on-hand if I need to replace anything else.
Everything Just Works (TM). I don't care if Linux is a wee bit more performant or supports a wider range of hardware. Truth be told, I simply want to do my thing & not think about the computer as such. I'm way past that age when "they say it's free, if you get it to run; the geeks say hey - that's half the fun!" (https://www.youtube.com/watch?v=d85p7JZXNy8) was a viable approach to computing.