Works for me most of the time.
I installed Winamp 5.5+ (I'm pretty sure there was a 7 and a 2 in there, but I don't remember *exactly* which one it was) into its own directory, and then moved/copied all the "old" stuff back in, as I saw fit. If I know it comes with the Winamp installer by default, I left it. Otherwise, I used the versions from my previous install. Annoyingly, this has posed a few problems, most of which are unimportant (If I attempt to rip a CD with Winamp, Winamp crashes).
Also, I think I'll remove the Media Library. It seems to cause issues with the title/tag display in the playlist. I think this is related to a combination of the Media Library, and having "Advanced Title Support" (or whatever it's called) disabled.
As for the buffering issue mentioned above, Winamp plays 1-2 second files just fine for me, so long as they are not the file I play first (they have to be in the playlist, and Winamp has to reach them as it goes through the playlist). I have my buffer settings at 5-10 seconds. Something really high. It makes the gap between songs much, much less (almost my entire library is accessed from within some kind of archive. I use in_zip a lot).
Honestly, perhaps I'm blind, but I can't think of any serious complaints I have with Winamp. In almost all instances that it's crashed, I've known the reason for it (usually it's my own fault. Often, however, it's crappy plugin. Most recent offender: in_skool/in_oldskool. It plays a ton of Amiga formats. When Knurek posted the Amiga Archive, I installed in_skool to see if it could play them. It plays most of them, but crashes if you attempt to do anything else...). Though, recently, I haven't used Winamp as much as I used to, and I only very recently upgraded to 5.5+ (I was using 5.5<something> previously). Maybe I'm just lucky, for once (odd though that may be). Mouser X over and out.
Guess I'll grab the pre-5.57x Winamp...
No, that colour scheme is what appeals to me, and it also prevents my parents from ever understanding or making out a single thing on my screen...
The fix is due to an issue that occurs when either installing Winamp, or running it for the first time (something it does to my mingw32-built dlls). If it still doesn't work for you in 5.572, try installing the fresh dlls (from this site) again.
I haven't tested any of this myself, though.
edited 2:56 PM EDT March 15, 2010
If you look CLOSELY in Winamp.ini you can see that the variable for this setting has the word "hack" in it, so yeah, it's just a shitfix that ends up breaking something else along the way...
It's best to keep the buffer as low as you can get it, otherwise, you'll have to deal with serious sound lag in EQ\DSP setting changes (obvious), BUT, also the memory\device viewer in NEZPlug++ and other things...