After some testing and ‘dialogue’ shared at Twitter, Daniel Kuropatwa says:
The winner is: Sendspace for simplest interface for non-techies to send large files to family and friends.
Sendspace gives you:
- Unlimited Uploads
- Unlimited Downloads per file
- Safe, Private, File Sharing
- Completely Free To Use
- Send a file to anyone, anywhere in the world, up to 300MB!
judyoconnell.com 
Hey Judy! Glad you found it useful too. There’s something to this twitter thing isn’t there. I’m still writing a post about our little community of (twittering) practice. 😉
Cheers,
Darren
BTW, Daniel’s my other brother. 😉