For what it's worth, I upgraded all three of my PCs (one desktop and two laptops) to the Anniversary Edition of Windows 10.
One laptop was already running Windows 10, the only one on which I was able to successfully install it earlier this year. A relatively new machine (2014), it took several tries to get it up and running.
With the availability of the Anniversary Edition, I figured I'd update the current Windows 10 laptop and the other laptop (2008) and desktop (2009) running Windows 7. I started the update last night, so that I'd have the weekend to recover if anything went wrong.
Unlike my initial attempts with the first releases of W10, this one went smoothly on all three machines. The trick is to start the update, then walk away. It takes several hours, the machine reboots several times, and if you sit there watching it, you'll go insane. "Just a few minutes..." can mean over an hour in Microsoft speak, depending upon your computer's processing speed, internet connection, etc.
So, what's it like, being up to date? Honestly, I don't believe I've used any of the highly-touted new features. It keeps bugging me to try the personal assistant Cortana, but until speech recognition becomes faster than my fingers and mouse hand, I'll stick with my current methods.
My major worry is about the continued usability of the old, 20th century 16-bit command-line console programs I use on a daily basis that originally ran under Windows NT or XP. So far, so good.
And yes, I've tried, without luck, to find conteporary replacements for those critical old programs. I'm waiting for the day someone uses on me the line I used when I was a software support rep: "I'm sorry, we only support versions released in this century."