Tvad - there's no reason you should be having to re-enter passwords every time the Mini goes to sleep, that's simply a matter of changing your network settings. Also no reason for playback to stop after the first song - a matter of iTunes settings. Darrell could likely take you through the process to fix those issues. I have a headless Mini with no keyboard or mouse that i control wirelessly with my MacBook Pro, and have neither of those issues.
If you prefer to enable the sleep function on the Mini, I find it's easiest to wake it up by pressing the start button on the back of the unit. If this is impractical with your configuration, consider that most folks simply leave theirs on all the time. I myself tend to turn it on and off once a day. Hope this helps - no reason you should be experiencing the hassles you describe - this setup is VERY plug and play!
If you prefer to enable the sleep function on the Mini, I find it's easiest to wake it up by pressing the start button on the back of the unit. If this is impractical with your configuration, consider that most folks simply leave theirs on all the time. I myself tend to turn it on and off once a day. Hope this helps - no reason you should be experiencing the hassles you describe - this setup is VERY plug and play!

