The setup is simple: You go to a website and are presented with a one megabyte file, ending in ".ZIP".
You unzip it and it becomes two files, one very small, the other much larger. The first ends in ".RAR" and the other ends in ".TAR". You unrar the first and it becomes ... a ".SIT" file. Oops, now you need stuffit. You untar the second and you get a file ending in ".ISO' That mounts in the desktop. Inside the ISO is a .BIN file. What do you do with this? You decompress the .SIT ... ah, it becomes a .CUE file. Okay, so...
You split the BIN with the CUE and you get a "multimedia" track, and a single "audio" track. The "multimedia" track contains one file, ending in ".ACE", but it's password protected. The audio track sounds like noise ... but you soon realize, no, it's just at a non-standard bit depth! Opening it as 8-bit gives you an even 120Hz tone on channel L... and some creepy noise on channel R. You look at it in spectral view and it's... letters. A password. So you un-ACE the file with the password.
Inside you find... an MP3, and a file ending in ".TXT" You open the TXT and recognize the header: It's a PGP-encrypted block. But where's the key? You play the mp3 file. WTF, it's 30 seconds of total silence! You're stumped until you look at the MP3 in a tag editor and discover: a PGP key in the "lyrics" tag. You try to decrypt the .TXT file with the key, but it asks for a password. After some blundering, you try the filename of the TXT file itself. That works, and you are rewarded with... A uuencoded file. THEN IT STARTS GETTING WEIRD.
Uudecoding the file gives you a file ending in .2MG. Arrgh, it's an Apple II disk image! You fire up Bernie and see two files: One ending in .SYS (research reveals this to be a Prodos 8 application), and one ending in .NES. WTF is a Nintendo ROM image doing on an Apple IIgs 800k disk? Booting into Prodos and running the .SYS clears the Apple II screen and displays a section of piano keys, labeled with letters, and a button marked "reset". Tapping keys plays the piano. Okaaayy...
Meanwhile, you SOMEHOW get the .NES file OFF the .2MG. Running the .NES game gives you what seems like a typical copy of Super Mario Bros 3. You play it for a few hours, wondering WTF the deal is. Eventually you get ahold of the Warp Whistle, but when you play it, the tune is different. This ROM has been hax0red. You break the tune down into notes, and play that on the Apple II... Which then grinds for a bit and spits you back to the prompt. You type "CAT" and see... A third file. Ending in .DOC. It's a Word '98-format document with a file attachment. WHEN WILL IT END?
You challenge is to design a puzzle like this.