Windows Feedback popped up on Windows 10 asking how likely I am to tell friends about it. I gave it 2 out of 5 listing three bugs (notification window doesn't open when clicked, can't right-click on Windows Store in task bar, customizing Notification Area dialog causes the dialog to crash), three bad features (no control over Windows Update, no Windows Media Center, and forget the last one), lack of USB Audio Class 2 Driver, and I called the Xbox app an "abomination" for PC gamers warning that if they keep it up, Steam OS is going to get very popular. I also said blankly that Windows 10 "feels rushed" and, that if Windows 10 weren't free, it would have suffered the same fate as Vista/8/8.1.
Which OS do I prefer? In my book, Windows XP Professional x64 Edition is still king. If it had DX12 support, I'd still be using it today.
I ran XP x64 for quite a while. My biggest problem was that driver support always seemed to be a few steps behind everything else, and getting the 8 GB of RAM that actually justified it on the DDR2 hardware it finished life with (yeah, support just ended last year, but it actually died when Vista came out and MS cut off anything but critical updates) was surprisingly expensive.
I've got the say Window 7 is probably my nostalgic best OS. Its 64 bit version didn't require sacrificing goats to get drivers, it wasn't absolutely horrible on the UAC side of things, the average user had enough configured for them out of the box to need very little maintenance, and MS hadn't started the nickle and diming micro-transaction OS model yet. Vista was a turd, 8 was for tablets only (which poisoned the well for 8.1, despite it being much better), XP had driver and hardware issues (really, it was released in the time of dial-up and lasted into 100 Mb internet so no qualms there), 10 was released too early with a myriad of issues that have yet to be resolved, and anything earlier than that just wasn't designed for a stupid user base.
As far as Linux, start with a major distribution, to test the waters. Debian and Ubuntu are good starting points. Once you've dipped your toes in there, determine what you want. If you're security paranoid, Backtrack. If you're footprint conscious, Puppy dog. I could list flavors all day, and not hit all of them. The amount of flavors out there is preposterous, and if none of the suit you make your own. Heck, with apt-get (or whatever variant your flavor uses) you can roll in anything you want, and expand any existing distro to be what you need.