WINE compatibility varies from program to program - "gold" rated (
Edit: it seems there's Platinum grade now, too) programs are good and everything else has an issue (or more). You can check that out at the WINEHQ website (
https://www.winehq.org).
WINE will mess with Linux's security architecture, though, and running windows programs in WINE opens up the possibility of Windows malware.
I prefer VirtualBox (but there's also KVM, VMware and others) to run Windows in a virtual machine. Programs run pretty fast (if you allocate enough CPUs and RAM) and you get the extremely valuable features that you can save the machine state, reset it, revert it, fork it, or clone it, plus with shared drives you can operate on files stored natively in Linux. One thing you don't get in a VM, though, is accelerated graphics, at least not with any stability.
I actually prefer most Linux programs to Windows variants, but there are some things I can't get on Linux (yet) like AutoStakkert2 for instance. Whereas I can and do use Libreoffice for all my home and personal document needs, I still occasionally proof a document in Word if I have to send it to a business where formatting is important ... sometimes there's a slight difference in font kerning or the size of a bullet point that will throw off tab alignment or pagination, though it's getting better. Libreoffice can open and save .doc and .docx files pretty well.
Updates and security on Linux are miles ahead of Windows. Miles! Though some distros are better than others.
What's a distro, I hear you ask? Very simply, Linux is a kernel (maintained by Linus Torvalds, a few other leading lights and many other talented teams and individual coders) plus a bunch of modules, libraries and utilities, and then a bundle of applications. The number of individual projects, small and large, contributing to Linux numbers in the thousands. It would be extremely difficult to collect ALL of them together. Plus, not all versions of programs are compatible with all kernels and libraries or even hardware. Take a project like Libreoffice - they code, check, compile and test in a handful of environments, then they make the source code available for anyone to use (and that particular project also makes binary executables available if you want to go that way).
A distro is a collection of software (including at least one kernel version and at least a minimum set of everything else) that is put together by a team, tested and distributed/released. Examples are Fedora, Ubuntu, Debian, CentOS, Mint, Arch, Gentoo, Mandriva, Bohdi, etc. etc. etc. There are a LOT of distros and different "spins" of those distros, and upgrades, and third party add-ons, and ... Using the Libreoffice example, the distro maintainers will take the source code and compile it against the libraries they've selected then test it with their kernel version(s). They'll do the same for hundreds of applications and utilities and, usually, several kernel versions. If they pick libraries and a kernel that are too old, newer apps might refuse to compile or load. If they pick libraries that are too new, older applications might break. It's a balancing act. They also make decisions about how well maintained and/or secure an application might be and whether it's the best fit for they're distro. When they've compiled and tested the lot, they'll put the main selection together in downloadable form (e.g. an ISO) and may (probably will) have some other less popular apps in online repositories (repos) that you can install from. Those repos are how you get updates as well. And you can add third party repos as well, if you want more apps, but then you'll need to be careful managing some compatibility yourself. (Most distros use install/update tools with automated dependency checking, so much of the work is done for you). I've had up to 9 add-on repos active but that did take a bit of juggling. Mostly you'll have one or two repos that are automatically set up during distro installation and maybe one third party add-on (like VirtualBox).
Good repo management (which is the default and to be expected in Linux) means all your updates are seamless - you'll get a pop-up/indicator that updates are available, and you click (and optionally enter a password) and they download and install ... about 20 times faster than Windows and usually with no re-booting. There'll be a reboot required if you update the kernel but some enterprise-grade Linux distros have even got around that problem with "live-splicing" of running kernels. I'm hoping those features will trickle down to regular distros in due course.
Some distros are better maintained than others. When it comes time to choose one, include in your assessment the frequency and quality of updates (and the pre-release testing). Sticking with free (as in beer) software, if you want "bleeding edge" and the latest versions, you might go with Fedora. If you want stability, maybe Debian (stable) or CentOS. A nice desktop and the closest to "works out of the box" might be Mint. The most customisable might be Gentoo. Of course, there'll be a million alternative opinions on that
. "Spins" are based on a distro with a different collection of applications, often specialised for a purpose, like gaming, video editing, software development and so on. You can still customise further, but most of the work is done for you by the spin creator.
Another thing to get used to is choice of desktop environment (and the vast array of add-ons and theming possible). There are at least 7 major desktops I know of, and I've used 5 or so at one time or another. Windows only has the one desktop, so it's an alien concept for most people. My favourite is Cinnamon, but MATE, KDE and XFCE are pretty good, IMHO. Gnome Shell and Unity are popular but not on my personal favourites list. Some distros only offer one
default desktop, but you can (almost) always install an alternative desktop manually - it'll be in their repo somewhere. Some distros offer a choice of desktop at download or at install time. From memory, Fedora and Ubuntu have the most desktops to choose from (that are in the default repos or in the ISO).
I changed to Linux a decade a go. Sure, there was a learning curve - though it's far less steep these days - but it was absolutely worth it and I've NEVER regretted making the change. I can liken escaping Windows to getting out of a bad marriage. Is it hard at first? Maybe, probably. Is it worth it? Too bloody right it is!
Linux is not perfect, but I absolutely love it.
Oh, and by the way, do you know where you'll find Linux? Well, about half the world's data centres and internet infrastructure, most embedded devices, about 95% of the world's supercomputers, autonomous vehicles, the military, the NSA, the ISS, and on about 2% of (the world's smartest people's) desktops.
