Re: I haven't updated my win 7 box in _MONTHS_
I, for one, stopped updating my home W7 box around the time when W10 was forced down on its users. I reckon in the event of an exploit it would take me less time to reinstall and restore, compared to the time lost with updates, reboots, loss of performance, loss of functionality etc. However, I am slightly cautious about what sites I visit, I mostly block JS etc. I am aware that this approach is not an option for company/work computers, or for computers used by less cautios people.
I do have a Linux machine that I use for most activities besides gaming and what little win32 development I still do. But I know from experience that Linux is still not yet ready for "the masses". And I'm afraid that when/if it will be, it might also be approaching Windows levels of un-usability. (Firefox is a good example of this tendency)
It seems to me that quite a lot of software - and Windows is a good example but far from the only one - tends to become increasingly user-hostile. Recently, when configuring a new (w10) computer for a friend I lost count of the number of hoops I had to jump through to avoid cortana, spying, edge etc. Not to mention additional hoops to uninstall the shovelware from both the manufacturer and MS.