Salvation or shell game? It's anyone's guess with Windows 10

Windows 10 will save us from Windows 8! But a look at upgrade paths and licenses will send you down the rabbit hole

communication maze digital communication technology 98187613
Getty Images

Living in my new yuppie-infested surroundings, I can really see what a strange breed they are. As a people, they seem irresistibly attracted to miniature dogs/barking gerbils and BMWs they can’t afford. Finally, what’s with the grocery store?

In yuppieville, there is only Fairway. Think Trader Joe’s on a Walmart lot. The place bills itself as an easier, healthier shopping experience through premade vegan quiche and 200 kinds of artisan cheese. Want Blistex? Too bad -- but try Allegra’s Recycled Hemp Lip Balm or DungFarm’s Macrobiotic Oral Therapy Stick (made with organically processed hemlock!).

Now I have to ride the Italian devil bike to Stop & Shop five miles away to stock up on non-organic reality. Bringing a six-pack of beer and a frozen pizza home on a motorcycle isn’t nearly as fun as it sounds. But at least I can use a savings card and I don’t lose 20 minutes of my life confounded by a surplus of aged dairy cultures.

I expect Windows customers must be feeling the same way, or at least they will be after the bloom bleeds off the Windows 10 rose. They've heard too many promises and face far too many choices. You’d think it’d be easy to choose – wait until Windows 10. But Redmond won't make it that simple; otherwise, their sales staff might as well take a vacation until the second half of 2015. One secret: upgrade paths.

You can't get there from here

There’s no direct path from XP to … well, anything. The hardware is usually too old for one thing; the applications are often incompatible, and the migration strategy is pretty much “from scratch.” The idea is to buy an interim license for another platform, then an upgrade to where you really want to get.

Going from Vista to Windows 7 is mostly direct and not overly complicated from a technical perspective, but it’s not so common nowadays. If you’re still running Vista, waiting for Windows 10 is a no-brainer. Windows 7 to Windows 8.1 is the easiest road today with lots of image engineering options, a number of app compatibility tools, and semi-clear edition to edition upgrade paths (7 Pro to 8 Pro, 7 Enterprise to 8 Enterprise). That will probably be much the same for Windows 10. Maybe that’s not too bad.

Then there’s licensing.

Wow, what a mess. I heard a pitch on the “new and simpler” licensing model of Windows 8 (supposedly being adopted across all Microsoft products) several months ago by a PR rep with a crocodile smile and suspiciously dilated pupils. Though I was sober, by the time he finished babbling I felt like I’d guzzled a fifth of Johnny Walker followed by a Quaalude the size of John Madden’s prostate.

Clear as mud

It may look simple in a press rep’s PowerPoint, but if you try and buy this stuff for more than 500 users, you either need special learning resources from Microsoft’s website (best read under the influence of Ritalin and off-brand Sudafed), attend a Microsoft Licensing Bootcamp (it's real!), or be smart and hire a licensing consultant monitored by the meanest, flesh-eating lawyer you can find. As with the operating system, there are too damn many variables.

Back in the Stone Age of pure desktop licensing, one user/one device was the mantra, though even then it was a headache. But now Microsoft and other vendors are pushing multiple devices per user. While Microsoft is trumpeting the myth of “one OS across all devices” (completely rapacious crap) it’s certainly not one licensing model across Windows editions (Pro vs. Enterprise) or versions (Windows 8.1 vs. Windows RT 8.1), especially when strewn across different device platforms.

Then there’s customer size. Small businesses get pushed to one licensing path and enterprises get pushed toward another with midmarket flailing in the middle. But in reality, customers can buy their Windows using any plan they want: Enterprise, Volume, Open, retail, and more. However, your smiling Microsoft sales rep sure won’t give you the right advice if the wrong words make her more money.

Now add companion licensing for that sweet multidevice sales scenario, virtual desktop and thin licensing for VDI and older devices, and all the CAL calculations for all the back-end server products you’ll need to run to keep all those devices happy. Windows Server and Exchange are the usual minimums, but more and more Lync, SQL Server, and System Center are wiggling in there, too.

Worm through all that and you’re still not done because here comes the crotch kick of hybrid computing, which means calculating ROI for per-seat numbers that now need to be combined or contrasted with subscription licensing. Are we using Office or Office 365? Is my server or desktop running on the box or in Azure? Is my salvation in a new job or a brimming shot glass? Now you understand why recently laid-off Microsoft sales reps are leaving the office with a spring in their step. Life is now a lot less complicated, and they no longer have to worry about red-faced customers keying their cars.

The upshot is that Windows 10 is nowhere near being a guaranteed fix for the cystic whitehead that is Windows 8. The reviews I’ve read make it sound like it’s already here and folks weeping over their new convertibles can wipe their eyes because Windows 10 will save us all.

I don’t know what that conclusion might be based on. Some new features and UI tweaks? A technical preview has only a small percentage of what we’ll get in the final feature set, and those have invariably been subject to change in the interim (read: disappearing like hobbits at an orcish orgy).

While the devil in those details can definitely frag the happy future promised with Windows 10, the devil in its as yet unreleased, and probably completely undecided, licensing and migration details is what will really send you slinking off to the local dive bar. Experientia docet, vini inungit.