NOTE: Running the ping command with the "-n" flag defines how many times the ping loop is excecuted. You might need to increase the number in "ping -n <number> 127.0.0.1" depending on the speed that your Vista loads so Winamp has time to start before the ping loop gets to it's end and itype.exe is started.
Why wouldn't you just use the "SLEEP" command in your batch program?
In any case, if anybody is looking for an answer, I've found that using the "classic" skin makes the media keys work fine.
I'm not sure what that has to do with *anything*, but it works. I've been doing that for about 4 months now.
Also, that would seem to indicate that it's a Winamp problem, not a Microsoft one, IMO. I just wish it would work, on it's own, without bogus "tricks" to get it work, with modern skins.