Hi Jason,
I can at least give you an answer for your first question. I use VLC media 
player. It can handle winamp playlists, and it can also be set as your default 
media application. It works very well, and is quite accessible.
There are a few check boxes that aren't labeled, but one's an EQ, one puts it 
in full screen mode in case you're watching a movie with it.
I hope that helps.

Friendly,
Chris

On Nov 8, 2010, at 8:27 PM, Jason SW wrote:

> Hello all,
> 
> I'm pretty new to this list, but not new to owning a Mac. I bought my iMac in 
> May, and since then I have also bought an iPod Touch 4G. However, I haven't 
> been able to totally switch over to Mac. One of the very few reasons I 
> haven't been able to stop using a Windows 7 VM constantly is iTunes. Compared 
> to Winamp, iTunes just seems horribly bloated and complicated. For example, 
> if I want to create a temporary playlist of only a certain subset of my 
> music, movies or TV shows, I have to create a new playlist and add all of the 
> files I want, whereas in Winamp, all I have to do is brows to the folder I 
> want to listen to, turn shuffle play on if I want to, and play it.
> The other thing is terminal applications. Especially when a lot of text comes 
> through, for example if I'm trying to use TinTin++, whenever new text comes 
> in, if Voiceover is already speaking, the speech is interrupted and the new 
> text is spoken.
> I'm just trying to figure out how to make this work, so any help anyone can 
> give me is greatly appreciated.
> 
> Thanks,
> Jason.
> 

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