I am with you. I am a sloppy dress for comfort type of guy. I don't need a fancy stylish watch.
As I said, I would like a device that:
would allow me to download music/podcasts without attaching to a computer
would beep each mile or other distance that I set before the run
Would show distance and pace so if I clipped it on my wrist I would be able to see it at any time.
Have the option to use it as a radio with both am and fm.
would keep track of miles and elevation - though I honestly don't know what I would do with that information.
Have a map that would show me where I am on the map so I could choose different trail options when exploring new trails
Would allow me to receive emails (it would vibrate or beep with a new email) and allow me respond to them with a voice message or convert my voice message into text and then allow me to send the email.
Allow me to use it as a gps device when I drive.
Allow wireless download of data from runs to my computer.
Size - the size of my current older generation ipod that I clip to my shorts and have no problems with it shaking around. The screen size is plenty big.