Re: Two questions...
What brand of keyboard do you use? If it's a Logitech or MS (or any other major brand name) keyboard, then you can download the latest drivers from their respective websites and it will work fine (I know for sure that it worked with Logitech and MS). I have a Logitech and it works great with Winamp5.
I'm guessing you have some generic keyboard that came with a computer package though. In which case, you may be able to get an update to make it work. Search the keyboard for a model number or something of the like and then run it through google.
I actually used to use WMP9 for a while for my playlists. and it has always kept what I had playing last (in this case, my playlist) when it started. I'm not sure what the deal is with yours. :-/
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