This is a rough collection of annoyances I've experienced while dealing with Windows or other Microsoft products. Whenever anyone says, "Well it's all just personal preference," I can just link them here and say STFU.

Installing multiple operating systems

There came a time where I wanted to have a laptop with Windows 2000, Windows XP, and Debian Linux installed on it - all on the same hard drive. With the size of hard drives these days, that's not an "unheard of" scenario. No, I didn't want virtual machines. I wanted to multi-boot. I wanted Windows 2000 because I play Worms Armageddon (yeah, old school, but still one of my favorite games) and Worms Armageddon just plain works better on Windows 2000 or Windows 98 than it does on Windows XP. I'm not sure what the underlying cause of that is, but that's been my experience. I wanted Windows XP because of all of the Microsoft OS's so far, that's the one I've had the most "stability" with, once I get it up and running (except, obviously, when playing Worms Armageddon) and there are still a few, choice things that can't be done in Linux. I wanted Linux because that's what I use to get most of my work done.

You might think, "Okay, multi-booting operating systems. That's not a difficult concept." I tend to agree! I figured, "Okay, just start sticking installation disks in, use the install processes to create partitions as needed, and you're good to go, right?" I started with Windows 2000. It very handily asks, early in the install process, on what partition you'd like to install. If there aren't any partitions, it allows you to create them. So, I figured I'd go ahead use that time to create the 4 partitions that I wanted:

1. 10GB NTFS for Windows 2000
2. 30GB NTFS for Windows XP
3. 1GB Linux ext3fs root
4. Extended
5. 19GB Linux LVM
6. Unpartitioned space

I know I said "four", and there are six items there, but trust me, only 4 of them really count

So, it installed as expected. Then, I installed Windows XP onto the 2nd partition. That worked as well. When I put Linux in and ran fdisk, it said that one of the partitions wasn't on a cylinder boundary. It turns out that the Windows partitioner ended a partition on one cylinder and started the next one on the same cylinder. So it was an off by one error.

• E-mail SSL: TLS in Outlook Express
• E-mail SSL: Accepting certificates not verifiable through a root authority
• GoDaddy SSL Certificate on Web server: Internet Explorer just says, " Internet Explorer cannot display the webpage" instead of saying what's actually wrong.
• Trying to uninstall a driver from Network adaptors in the Device Manager yielded "Failed to uninstall the device. The device may be required to boot up the computer." I know damned well that it's not required to boot up the computer. There are no other indications as to why it can't be deleted or why it "thinks" that it's required to boot. Googling for suggestions mention a bunch of things, none of them worked. Meanwhile, it's trying to install the same device that's already listed and then just says, "Cannot Install this Hardware. There was a problem installing this hardware: Broadcom NetLink (TM) Fast Ethernet. An error occurred during the installation of this device. A device attached to the system is not functioning." That gives me a whole heap of information (not). "An error occurred" "oh. Well, what was it?" "IT WAS AN ERROR!" ":["
• Mounting a hard drive from one computer as a secondary drive in another to do a backup. Logged in as Administrator, some files won't copy because they aren't owned by Administrator and there aren't any permissions on them except for the owner. You can't see who the owner is, but you can re-own them to someone on the system reading the drive - fat lot of good that does when you're planning on putting the drive back into the original computer when you're done. But, the most frustrating part about this process is that when it gets to one such file, the ENTIRE copy process halts due to the error instead of just informing you that there was an error and moving on.

Other random thoughts/bullet points

• When your troubleshooting model lists "reboot" near the beginning of the process, there's a problem with the design
• So much more can be done with far fewer resources using just about every other OS. For instance, a base Debian install plus Apache, PHP, PostgreSQL & MySQL uses somewhere between 400 and 600 MB of drive space. A base Windows Server 2008 with IIS, ASP.Net & MS SQL is about 40 GB. Sure, you could do a command line only installation of Windows that takes up far less than that, but in reality, how many times do you see those in production? Why? It's a major pain in the butt to administer a headless/nonGUI Windows installation
• Installing software - if it installs other software but puts that installer dialog behind the first one, and you don't know why the first installer stopped installing because it's waiting for the second one to complete in order to continue. This happened to me while installing wireshark and it installing the pcap stuff