I want out of Windows patch hell

The only path out of Windows patch hell is Linux and Mac OS. If you're not already migrating every app you have to the web you're either a masochist or delusionally thinking Microsoft is still focused on delivering a decent desktop experience.

For the latter group I have news for you: Microsoft is going "all in" with their "services" strategy. Operating systems and fat client software don't exactly fit neatly into the "service" model.

The future of Microsoft is as a competitor in a commodity cloud services market. The thinking is that they can provide value in the form of commercial web applications like Office 365. In other words, they think they can do a better job than Google and Zoho at serving enterprises things like email and spreadsheets.

You know what? They just might be able to do a better job. Especially if they actually put in some effort into supporting non-Microsoft platforms (e.g. web browsers other than IE on platforms other than Windows). They also have to a long way to go in terms of federation so businesses can work with each other without compromising security.

In the end though, I think it is pretty clear that Windows isn't going to be Microsoft's focus anymore. I expect they will allow the platform to slowly erode away, collecting as much revenue from it as possible while converting their business to services.

Patching on Windows 7 is just as bad.

I let my Windows 7 PC go several months without updates, because it seems like no matter how many I did, there were always more when I restarted. So I finally had a brief scare with a file (opened up something inside a rar package that was disguised with a .jpg extension but was an exe) and decided I needed to get up to date.

It took a week of updating before my damn computer was done with them. I had over a hundred packages to install, but I wasted several days where they would show as being available, yet when I would try to download them, the progress bar sat at 0% for hours without ever moving.

A few days of googling and trying again, I finally got a few "roll-up" patches to install (which still required leaving the computer alone for 24 hours, mind you), and then I was able to actually get the rest of them to download. Restart and all is well, right? Nope. As soon as they were done and I restarted, I was informed that I had a dozen new ones to grab. Download, install, restart. Rinse, repeat. At least four more times. It was absolutely ridiculous.

His characterization of Current Branch for Business (the 'Defer Upgrades' toggle in the Update settings pane) as blocking security upgrades for a year is a bit off the mark.

CBB defers major feature upgrades, like the Anniversary Edition which started rolling out recently, but you continue to receive updates for the build you're on -- including security updates. You'll eventually receive major upgrade build N when build N+1 has rolled out to consumers, and when N+2 rolls out, N becomes unsupported.

This option is only available for Pro and above, so Home users are essentially stuck in permanent beta-testing mode.

It's funny, we expect "undo" features in our applications these days, why shouldn't the OS and indeed the entire machine's state be treated the same way?

I used to think that virtualized Windows guests would eliminate the need for wine. I have XP and Windows 7 VMs around precisely for games or the few applications I use that aren't wine-friendly. Over time my usage of wine has dropped to the occasional Play on Linux game.

But part of what makes those VMs so robust is that 1) they're normally disconnected from the internet, and 2) I have developed a habit of saving my work to a shared folder so that I can reset a machine's state to a few days previous at the slightest sign of trouble. For applications that require access to the internet, however, wine may be our last, best hope of opting out of the Cortana Empire.

Historical aside: Before VM usage took off Robert Shingledecker and friends followed that reset logic to an extreme with the Tiny Core Linux project -- every time you start your machine you load a known-good kernel and apps into RAM, use the machine, and then let anything other than your data derez at the end of the session. You can get pretty good performance with that approach on older hardware that can't support virtualization. The downside is that your application choices are limited and dated when compared to mainstream Linux distributions.