Old OSes in the modern world
For now, let's let "OSes" refer to Windows and Mac. I know Linux is a complete mix of versions with this, so it may be easiest to leave it out of the question.
The question is: What is the oldest operating system that can be comfortably used for at least most of your computing needs?
For me, I think the answer for my school laptop might be Windows 2000. Given the laptop has full Windows 2000 drivers, it can be updated officially through 2010 from Microsoft Update, and some folks online have been continuously converting XP kernel patches to Windows 2000, meaning it can run most "XP and up" software (For the rest of this post, we'll assume these unofficial updates are installed.), including the newest versions of Opera and Firefox. Chrome is buggy, IE tops out at 6, and I have no idea about Safari. The newest Flash can be used, and a lot of somewhat-recent games work as long as you have the graphics card (and drivers). Yes, Minecraft works, arguably better than on 7. GIMP seems to fare nicely. The OS works great as a media player; MPC-HC, VLC, pianobar, Winamp, and many codec packs work fine. OpenOffice works fine, but if you're a Microsoft Office fan like me, you'll need to do a lot of fudging with Office 2007/2010 to get them to work. 2003 works fine natively, though, as should the 2007 compatibility pack for newer files.
Windows 98 would practically be desktop-only, unless you get very specific drivers for your old Wi-Fi adapter, which likely wouldn't support WPA/WPA2. Even then, your best bet for browsers is Opera 10.10. I don't believe any browser newer than that will run on 98. 98 itself has KernelEx, but it's largely unsupported, and very few modern programs still run on Windows 98.
Anything before 98 would have to be a specialty machine with one very specific purpose. The unofficial MS-DOS 7.0 can work fairly for a music player, for instance. (A system I used to have could play MP3, WMA, WMA Pro, AAC, OGG, FLAC, WAV, and a couple other formats.)
I know fairly little about Mac OS, except that there are two critical points where nothing before and nothing after were compatible: between OS 9 and OS X, and between PowerPC and Intel. If you have a PowerPC Mac, you're practically out of luck with any new Mac software.
At the moment, I'm planning to get a larger hard drive for my laptop and dual boot 2000 and 8 to see if it's doable. (Currently, I have 7 and 2000 in dual boot.)
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