Should we take the free Win10 Home upgrade or pay for Pro?

Excellent question from BA:

I am on Windows 8.1 & the main (really only) reason I want to upgrade to Windows 10 is for Cortana.

However, since Automatic Updates can bite (& thanks to you I don’t let Windows do them), I’m concerned about the free upgrade.

Since this is Win 8.1 Home, the free upgrade would have to be to Win 10 Home & the only way to control automatic updates is through the metered connection workaround. I know that if I upgrade to WIndows 10 Professional for $99 I have more control back. What do you suggest?

1) Take the free upgrade & use the workaround to (hopefully) escape getting bitten in the butt?

2) Pay the ‘update tax’ of $99 for Win 10 Pro?

3) Let the free upgrade expire, stay on Win 8.1 & pay to upgrade at a later date?

I hoped you would give more definitive advice sooner as we got closer & Microsoft wouldn’t relax the deadline for free upgrades. Hope I hear something before Friday.

I have an InfoWorld post coming on Monday morning, going over the upgrade options and sane alternatives, but you raise some interesting questions that I don’t cover in the main article.

First, if you’re looking at upgrading to Win10 for Cortana, make sure you try Cortana before you make the commitment. I found Cortana to be distinctly underpowered, especially compared to Google Now (which I use frequently), but also compared to Apple’s Siri and even Amazon’s Echo. You can compare them for yourself. Try using Google by going into the Chrome browser’s address bar and clicking the mike. Test Echo at the echosim.io site. I don’t know of an easy way to test Siri without finding somebody with an iOS machine, but they aren’t hard to find.

I wouldn’t pay extra for Pro just for the convenience of blocking updates. There are other methods, besides metered connections. At this point – call me astonished – the Win10 cumulative updates have been relatively benign. If Microsoft proves that it can’t update Win10 any better than it’s been updating Win7 and 8.1, you’ll always be able to pay for the upgrade to Pro.

I talk about the pro’s and con’s of running a free upgrade now and rolling back, in the article on Monday morning. Basically, for most people, it just isn’t worth the effort. But if there’s a Win10 feature that you really, really like – yeah, you should probably grab your free digital license. If you do, though, be smart about it and don’t just blindly run the upgrade.

Anyway, more details in the article, but for now, you should really think about whether Cortana is worth the upgrade angst.