The unbearable misery of upgrading to Windows 8.1

There are some events that we humans know from experience will be painful: Childbirth, passing a kidney stone, or getting a colonoscopy without anesthesia. After last weekend, I can now add, without hesitation, upgrading Microsoft Windows. I've been doing Windows upgrades since Windows 3, and it's always been relatively straightforward: You either do a straight upgrade that includes everything, or you do a clean install of the new version, restore your files and reinstall your applications.

Things got muddled with Windows 7. I, like many people and companies, decided to skip the abomination against nature that was Windows Vista and stay with Windows XP. That turned out to be the right decision, but when Microsoft introduced Windows 7, even though it really wanted XP users to upgrade, it prohibited direct upgrades from XP. That meant that XP users could move files, folders and some settings over to Windows 7, but they had no choice other than reinstall all of their applications. In my case, I had a huge number of applications that had accumulated over the years that I was running XP. So, I nursed my old system along until last winter, until it was just too slow to be useful any more, and then transferred what I could to a newer PC running Windows 8 and reinstalled my apps.

Then came Windows 8.1, specifically the Windows 8.1 Preview, which I installed when it was released. I hoped that Windows 8.1 would solve some of the worst problems with Windows 8, starting (no pun intended) with the Windows Start menu. Although the Preview never fixed the Start menu issue, it did resolve some of Windows 8's other aggravating design flaws. However, when it came time to upgrade to the final release of Windows 8.1, the Preview turned out to be much more trouble than it was worth.

Here's a step-by-step summary of the update:

1. Bought a new Toshiba Satellite laptop with a current-generation Core i7 processor and 16GB of RAM to replace my old Samsung first-generation i3 laptop.
2. Installed the Windows 8.1 Preview on the new machine to make it simple to transfer everything from my old machine to the new one.
3. Learned that Windows 8.1 Preview cannot be updated to the final release version of 8.1 without having to reinstall all the applications, so I put everything on hold for almost a month until the final version of Windows 8.1 was released.
4. Last weekend, installed the final Windows 8.1 on my new machine from the Windows App Store.
5. Found that I couldn't install the final version on that machine without a serial number, and it would cost more than $100 to get one, so I figured out how to roll the new machine back to Windows 8. That also reinstalled all the crapware I had removed from the machine, but at least it allowed me to install Windows 8.1 for free.
6. Purchased a to-remain-nameless PC transfer program and installed the program on both machines. The software required that I uninstall all Norton software from both PCs, so I got all of the Norton software off my old machine, and all the preinstalled Norton crapware off the new one except for one anti-theft program that failed to uninstall.
7. Ran the PC transfer program, which failed instantly with a cryptic error indicating that the registry on my old machine was corrupt.
8. Sent diagnostic file from old machine to vendor of PC transfer software, and received reply saying that I had to send diagnostic files from BOTH machines, even though there was no way to do so from the old machine using the vendor's program, and oh by the way, I still had some Norton software on the new machine, and I had to remove ALL OF IT.
9. Manually removed every remaining Norton-related file I could find on the new machine and tried the transfer again. It again failed instantly with the same cryptic error.
10. Checked the registry on the old machine and downloaded software to send a diagnostic log from that PC to the transfer software vendor. Sent diagnostic logs from both machines. Received a reply the next day from the same tech support engineer that was word-for-word identical to the previous one, except that he highlighted the note that I HAD TO UNINSTALL ALL THE NORTON SOFTWARE.
11. Reinstalled Norton on the old machine so that I had some protection on the Internet, then purchased and downloaded a copy of Laplink PCMover Professional. Installed PCMover Professional on both machines. Threw the unnamed transfer software into the garbage.
12. PCMover's documentation was much less cryptic than that from the unnamed transfer software, but it required me to disable a fair amount of software (Internet security, backup, defragmenter, scheduled tasks, etc.). Disabled everything relevant I found on both systems and started the transfer.
13. The transfer took about six hours, but it worked. All but a handful of programs from my old machine transferred over, and PCMover was very clear about what it could and couldn't transfer.
14. Once I started working on the new machine, I found out that not everything that transferred worked as expected. For example, Google Chrome worked fine on the new machine, but it couldn't update. The solution was to remove all my Google applications, wait an hour, and then reinstall them, which fixed the problem.

Step 5 started last Friday evening; it took me to Monday night to get through Step 14. So, what are the lessons to be learned from this experience?

1. Never install a Windows Preview or Beta version on your primary PC. Even if you're a developer, load it on a PC that you can afford to wipe when the Gold Master or Final Release is available.
2. Use Laplink to do the system transfer when you're not doing an in-place upgrade, and avoid transfer software from companies you've never heard about before, even if they have good reviews. You don't know if those reviews were paid for.