I watched somebody struggle with their Macbook for an hour and a half yesterday. I'm a Windows power user and a member of the Insiders program (meaning I test Windows 10 builds before they're released to the public), so I know how to troubleshoot things.
But I have, quite intentionally, never learned how to fix Macs, or any Apple device. Because I've gotten sick and tired of Mac users telling me how it "just works" and they have "zero problems".
That's a bald-faced lie. Computers are incredibly complex machines. There were always be problems. But the elitism of Mac fans means I don't really want to help them navigate it.
(She was having a very basic missing driver issue, by the way.)
Here's the boilerplate advice I'd give to
@kithnou or anybody else asking if they should upgrade at this point. If you're happy with your current 7 or 8 setup, really aren't excited about any of the new features in 10, aren't enough of a techie to want to play with the new shiny stuff, and think you might possibly buy a new computer before June anyway, don't worry about it.
There are added advantages in security, startup time, and efficiency over 7 or 8, but none of that is Earth-shattering. If you change your mind, the free upgrade is available for a few more months.
The biggest advantages, like access to the Windows Store apps or enhanced touch support, are things that are still very much under development or only apply to newer machines anyway.