@dew7: I personally use Windows because it runs all of my games hassle free. I once dual-booted with Linux for a semester of class work, and I frequently use Mac OS X to develop iPhone applications. As far as the most secure OS goes, that would have to be the
open-source one (Linux).
I've come into an easy malware-free life with my Windows XP system using simple methodologies on safe web surfing and file running. I use Firefox with the NoScript plugin. I have NOD32 Antivirus running at all times. I scan every new archive or executable that I download. I wasn't aware there were plugins that alter data-mining information. I'm definitely going to look into that. I haven't had a virus on my computer in over 2 years.
You'd want to move away from 9x for nothing else than to get away from the FAT32 file system. In this day and age, we have gigabytes of RAM and terabytes of disk space. FAT32 is just a bad choice for modern computers (if that's the route you're going). I am under the impression that people have hacked a more modern file system to work with 9x though.
Privacy is a huge issue. Facebook lets you tweak all your privacy settings and has lately been actively trying to walk newbies through the process. At one point in time, pleaserobme.com raised awareness to the growing issue of privacy by actively posting Twitter tweets from people describing their whereabouts. There have actually been robbery victims who accepted Facebook friendships at random (and the robbers turned out to be amongst those "friends"). This is a serious issue that will never be solved--only made more apparent to everyone.
Personally, I use Facebook, but I made different Friend groups (labels) and assigned privacy levels to each one. I never talk about where I am or where I am going to be at.
Google completely anonymizes your logs after 18 months. A year and a half is still enough time to do some over-zealous self-detrimental Googling, but it comforts me to know that 20 years from now, people won't know what I searched for on May 1st, 2010.
The thing with requiring a license... I do not believe you should be required to retain one to use a computer or the Internet. For driving, you are required to have a license because you could easily kill other people if you disregarded several signs, rules, and laws. With an at-home computer, the only person you could potentially harm is yourself. Now, you're going to have to cut me a bit of slack here. I am fully aware letting viruses, trojans, and malware infect your computer to help run as a distributed system to take down multi-billion-dollar corporations or national security systems would easily cause harm to others, but that is not within the scope of this question as far as I was aware. We are wondering if people should be required a license because they too easily give away their information. I would sooner require people to own an antivirus subscription than a know-how-to-properly-use-computers-and-the-internet license.
Check this for a second. If we required them to retain licenses so that, for all intents and purposes, we trust them to be smart with their sensitive information on their computers and the Internet, then they should be required to retain verbal conversation licenses as well. Social engineering is MUCH more effective than brute-forcing somebody's password.
As far as Apple and Adobe goes. I hate how militant Apple is. I've really grown to hate them. Adobe on the other hand gave me James Cameron's Avatar with their Creative Suite. I love them for that, but they do have security issues. I don't have Adobe Reader installed and use FoxIt Reader. Although, I don't stay away from it for security reasons. I just feel Adobe Reader is CLUNKY! Also, Adobe Photoshop CS5 has
content-aware fills. Whoever designed that algorithm deserves my first 2 children.
How could you not like USB? Shame on you!

I'm just teasing. I actually love USB for its convenience. We really have no use for floppies these days
except for old businesses that still use them for old systems. Anything further than that is just pure hobbyism. Flash Drives serve all of the floppy disk's purposes (on modern machines--which is all normal use entails) with MUCH more megabytes (
gigabytes) of space. Oh wait, they can't be used as a coaster.

Haha. I'm joking again. As far as hardware for Apple computers goes, several Macs these days use nVidia cards and Intel Core 2 Duo chips, but I agree that I don't believe you can customize the hardware like you can with a PC (although, I've never researched it to see if it's possible or how easy it would be).
@Delling: I remember watching that. I believe a point system for non-sensitive things will definitely arrive in the future (such as the toothbrush), but for obviously important stuff, it will NEVER happen! Wait, scratch that. It COULD happen right before the Earth's next apocalypse--which would coincidentally be the cause of said apocalypse...
Anyway, thanks for letting me geek out for a moment. I look forward to further discussions.