Setting up Windows 95 to browse the web could be a bit tricky since it's so old, but Windows 98 should be a snap. I don't really have anything against the idea of browsing the web using those systems: at this point, they're so old that modern worms and viruses aren't compatible with them... and I'm not even kidding! Install Firefox 2.0.X (3.X doesn't support Windows 9X), and you should be on your way to run something stable and relatively modern.

At their core, the server versions of Windows share many elements with their consumer-oriented brothers, except that you get less multimedia features and more hosting-related systems. I don't see why it wouldn't run properly under Virtual PC.

I'm not so sure in this case, it depends where we'll be. If an eventual Windows 8 uses a brand new core for it's operating system, we should be safe. If it's still in the NT line (which includes XP, Vista and 7), then many of the vulnerabilities will be shared. Windows 98 is from a completely different product line, so the potential exploits are not the same as what we get now.