My Linux journey started way back when it was CLI only & X was just being born - in those days it was normal & expected to do everything via command line because all there was worked that way (the DOS era...).
Kept watch all the years between then & now and after everything got 'windows-ized' it was obvious to me that user's expectations had changed radically & that for Linux to be a viable option for more folks - it had to be doable via GUI & user-friendly (as in non-threatening) to the user's POV.
It finally reached that point a few years ago - right around when Android had begun to change, well...everything really.
Like it or not - Linux is by now already dominating the IT world whether folks wish to notice that fact or prefer not to see it.
Part of that dominance was (thankfully) driven by how M$ totally lobotomized all their products since just after XP.
So here is my own take on the best options for myself in the present time, OS-wise:
Familiarity & minimalism in the OS & GUI are requirements of mine - they have to be functional AND undemanding of attention - I always compare the OS to the foundation of a house - not something we should bother with much UNLESS it DEMANDS attention to remain solid so as to hold the rest of the stuff up reliably.
Both of my requirements are well met by Ubuntu Mate LTS - as long as that horrid Unity abomination is immediately removed.
WINE can be something of a PITA, but adding PlayOnLinux can be a big help if one has needed apps that are reasonably well suited to use that way (http://www.playonlinux.com/).
Since I have things that run best in their own OSes, I prefer to use Linux as a host OS, add in the free VMWare Player, and use a VM (made via P2V of my prior configuration) of XP as well as the old AndroVM.
This way I have familiarity in my minimalistic OS choice as well as faster than native usage of the 2 other OSes & their apps.
Most likely that all sounds overly complicated - but really all it took to do it was some searching, a little bit of learning & an even smaller amount of trial & error to get it set up well.
Lastly I wish to mention that when (IMO) Linux finally became Grandma & Grandpa friendly, 2 amazing things happened for me:
The 1st was setting up an 80+ year old friend with a variant of Ubuntu 11.04 LTS to replace XP - and that still serves him well every day maybe 6 or 7 years later - truly problem free & he is a total technophobe.
The 2nd was when I helped another friend who is in his 30's, but who was computer illiterate by his own preferences into a similar OS situation - only he also needed some windows software for his business besides...so=>
Enter VMWare Player and a windows VM for his needed apps.
Now he has been using that configuration for years already - and the only problem he ever had was when he got a different monitor & botched up changing the resolution - which required a little help from me - but that was the ONLY time ever since the beginning.
The main gain that windows users can get from moving into Linux on their PCs is lowered stress IMO;
This comes from its incredible reliability coupled with an absence of pretty much ALL the irritations which are so normal & accepted without question by most windows users...like:
Data losses...the need to be ever vigilant for trojans, viruses, other malware and even ransomware...endless scary updates that often break more than they ever fix...forced 'upgrades' necessitating changes they'd be happier without...etc., etc...
The tired old saying that says:
'Better the devil you know than the devil you don't know'
Applies totally in this matter - as it mostly fear of changes that keeps folks from making such a really good change.
Really funny to me is that it is likely that many folks would see the title of the video I posted here at the top - and without even viewing it (or maybe just a few minutes of it at most...) would conclude that Linux MUST indeed suck !!
A shame that NOT ONLY is the opposite of that both factual & true - but also that most of those very same folks likely spend much of their days using Linux on their smartphones without even knowing it.