Windows 10. Should You Upgrade and When?

Update: 
As I was completing this blog, I received a newsletter addressing the new (and ever changing) Microsoft licensing as it applies to Windows 10. Microsoft's licensing structure has always been very confusing to me. For their OS, they have so many levels and versions, and so many caveats that it takes an expert to even fake understanding it. The "free release" of Windows 10 makes it even more confusing! See, when you buy a computer with a Microsoft operating system (OS) on it, you don't really own the operating system. You purchase a license to use the OS. So, it is not your property (except in certain cases which most people would never use). In addition, when you upgrade your computer (such as adding a new hard drive) you have to call Microsoft and get your license renewed or it will not function properly. If your computer dies and you buy a new one without an operating system, you CAN NOT use the OS on your old, crashed computer to install on the new one (unless you have a full retail version of the OS only). All of this licensing mumbo jumbo applies to the current crop of Microsoft operating systems.
So, what does that have to do with Windows 10? Well, the free upgrade of Windows 10 just adds another layer of complexity and confusion to an already convoluted method of keeping track of your license to use a product from Microsoft! 
After reading the newsletter (written by an expert on the subject), it is clear as mud. So why did I include this update? Just to let you know that even if your Windows 10 upgrade goes smooth and works properly you could run into issues later on down the line. 
What kind of problems? Consider the following:

• You upgrade your computers hardware and have to re-activate your license.
• Your computer crashes and your have it rebuilt, requiring re-activation.
• You have to reinstall the operating system (this could be a nightmare)

I want everyone to be forewarned that issues could come up later if something goes wrong and you need to make repairs (either hardware and/or software) to your computer that has been upgraded to Windows 10. 

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By now, most of you have heard that Microsoft has released a new operating system called Windows 10. Many of you have even noticed the "Upgrade to Windows 10 For Free" icon in the system tray. I thought I would address this latest release from Microsoft and give you a few tips on how to upgread, when to upgrade and how to prepare to upgrade.

First, Microsoft has been working furiously on Windows 10 in order to get it released as soon as possible. Why? Because Windows 8/8.1 was the worst operating system Microsoft has ever released! Period, end of story! Even Windows Vista was head and shoulders above 8 (and that's saying a lot). They knew they had to come up with something better and they had to do it quickly. So after all the firings, hirings and restructuring at Microsoft, they got busy on Windows 10.
So, why is Windows 10 free? A few reasons: They really messed up on Windows 8/8.1. They figured they better do whatever they could to retain and/or reel back in their loyal customer base. Plus, technology is changing and Microsoft finds itself in a peculiar position. They are making huge changes to their business model in order to compete.

Enough history. Now, Should you upgrade to Windows 10 and if so, when and how? The answer to this question is, yes you should upgrade especially if you are running Windows 8/8.1.
But, not so fast! You have until June 30th, 2016 to upgrade. So, here is what you should be doing to prepare for and complete the upgrade process.

First, you should wait. You don't want to upgrade the minute a product comes out. Especially if you are running Windows 7 (a perfectly capable and stable operating system). You should give Microsoft a few months to release updates and bug fixes before upgrading. No need being bug testers for Microsoft. Let them shake out the problems then you can proceed with the upgrade.
Windows 8 users should upgrade first. Let's face it, you are the ones in the most pain and need some relief. If you are running Windows 7, I wouldn't be in a hurry to upgrade. Give Microsoft enough time to sufficiently release updates, bug fixes and drivers.

When you get to the point that you feel it is time to upgrade, you want to go over a few things to make the process as painless as possible. Here is what I would suggest before attempting the upgrade process:

• Make sure you have a good backup (or two) of your data. It never hurts to assure you have all of your files successfully stored on an external hard drive or DVD.
• After making a good backup, it would be a good idea to delete any unused file on your system. As long as you have a backup and you no longer use the files, no need to keep them around.
• Uninstall any software you aren't using. This is a good tip for any user, but especially if you are going to be upgrading.
• Complete all of your Windows Updates.
• Do a thorough virus/malware scan of your system.
• Turn on system restore and create a good restore point.
• Make sure you have plenty of hard drive space.
• Make sure you have your Windows 7/8 product key available (just in case).
• Do your research on Windows 10 first!
• Now, read some more (it won't hurt)!
• You might want to download the installation media just in case!

When you start the upgrade process, allow enough uninterrupted time for the process to complete. As a note, I wouldn't start the upgrade at any point when you think you might how power interruptions (weather related). It is never a good thing to lose power while doing any kind of upgrade and/or update. So, if you see a huge thunderstorm churning in the distant, find something else to do!

After you have completed the upgrade process and you boot up the computer and log in for the first time, you need to take time to do an initial check of your system. Everything could run smooth and you might not have any problems. Some issues might not surface for several days or weeks. However, check the following to insure your base system is functioning properly:

• Open Windows Explorer and check that you can successfully navigate all of your file system. Go to "My Documents" & "My Pictures" and check to see if all of your files are intact. If you have external drives attached to your system, check them as well.
• Check to see if your printer is still recognized. If so, try to print a document. 
• Open your most frequently used applications to insure they work properly.
• Insert a USB thumb drive to see if you can access it properly.
• If you transfer photos from a camera (or a smartphone) to your computer, try the process with some test photos to see if the process works properly.
• If you have multiple accounts on your computer, try logging in to each one. 
• Run Windows update.

At this point, if everything is working properly and without any weird glitches, I would say you have a successful upgrade! But, don't be surprised if you experience some weirdness down the road. Especially with hardware drivers. When a major OS is released, it takes a while for the drivers to be updated, so you just have to deal with it. Just make sure you stay current on your Windows Updates! It is also possible to have some issues with older software as well.

I'm sure some people will think all of this reading and planning is overkill. It might be, but I would rather be prepared and have a successful upgrade that a half-hearted effort with questionable results. Poor planning is usually just asking for problems.

I must mention upgrading from Windows 7. There is really no technical need to upgrade if you are running Windows 7. Windows 7 is probably one of the best operating system Microsoft has ever produced. The only real reasons to consider upgrading from Windows 7 to Windows 10 are:

1. Microsoft is offering you a FREE operating system!
2. Each Microsoft OS has a lifecycle. Windows 7 is good until January 14 2020. Windows 10 lifecycle ends on October 14, 2025. So (on paper at least) upgrading buys you 5 extra years.

Let's be honest about the above information. Do you really intend to keep your computer for FIVE MORE YEARS????????????? Really? Plus, in the case of Windows 10, you are looking at 10 more years. Looking at either set of numbers, it really doesn't make sense to upgrade Windows 7 to Windows 10. HOWEVER, Microsoft has made their move. Windows 10 is soon to be the latest of their operating systems. That kinda forces the end user to switch. Sure, you can keep Windows 7 and it will continue to work fine, and you will continue to get updates. But, you won't be running the latest and greatest. You will soon only see mentions of Windows 10 when referencing a Microsoft OS. So you might as well upgrade. Besides, most people will be buying another computer before these licences expire.

Remember, Microsoft released Windows 10 to replace the poor excuse of an operating system called Windows 8! Windows 7 doesn't need to be "fixed".  

In closing, don't get nervous and worry that you are going to miss the boat. Give Microsoft a little time to get the bugs ironed out, then start the upgrade procedure.