1. Who makes the best MP3 Player?
Apple has always had a good emphasis on the user-experience, but their mp3 players were not superior enough to competing offerings to overcome their closed nature (e.g you have to use iTunes to load your iPod). However with the avent of the iPod touch their superiority over other players is now a matter of them being a vastly different device. It's not just an mp3 player, it's a 1999-era computer in your pocket.
Right now, the iPod touch is a no-brainer, but the iPhone was created for a reason. The phone will be the convergent device. People aren't going to carry a phone, a PDA, a digital camera and an mp3 player when it can easily all be one device.
So with that in mind, I'd say the best mp3 players right now are the iPhone and their main competition will come on the phone platform (e.g. the Nexus One has better hardware than the iPhone right now).
2. How many MP3 Players have you owned/currently own?
I've owned dozens, right now I'm not sure how many I own (I have a lot of old mobile gadgets in a box, most play mp3s) but I really only use my phone for a portable mp3 player.
3. Does your MP3 Players play video?
Yeah, but I'm not that into that.
4. Does size matter? What size is your MP3 Player?
Both physical size and storage capacity are some of the key factors in a portable mp3 player for me.
Right now my phone is 8GB and I am constantly removing apps and don't have enough space (I'd love to spring for a 32GB new iPhone right now, but that would set me back over a grand down here in Costa Rica and my newfound fiscal maturity is getting in the way of my inner geek).
5. Do you use your MP3 Player as a portable hard drive (to transport files other then music or video files)?
No, the cloud pretty much killed my need for portable storage. Right now the key is having a data connection and your files on the web and they are available everywhere.
6. Is your MP3 Player your smart phone?
7. Dream of a future feature that might be on the next/later generation of MP3 players. What would that be?
The death of the mp3 format and the adoption of a superior, open-source, format. Right now mp3 is not the best option for music quality, but it's the best option when it comes to music portability (everything plays mp3s but no other format is as universal).
8. Any MP3 Player horror stories? Toilet drops? Kidnapped by fiendish greasy-fingered thieves? Ever have to kill a man with your knockoff iPod Shuffle?
I once walked into a favela
(shantytown) with one, and some drug dealers tried to rob me (they were new at the time). But others intervened and told them that I was from a nearby neighborhood and you just don't go cannibalizing your own hood (honor among thieves). I eventually became friends with them and gave one of them the player when I left town.