This is going to sound like an odd question but the general consensus it seems is that the last BEST version of Winamp is 2.9x. The 3.x and 5.x versions are overloaded with uncessary clutter. The problem is I cannot figure out the "x". I just want to be sure I am running the best version of Winamp I can. BTW, I am a Foobar user but sometimes I like WA for stuff.
Winamp 5.x lite is essentially the continuation of winamp 2.x, I would harldly call it bloated, it doen't support modern skins, play video's, or even have media library. It doesn't do much besides play music. Plus, the newest version comes with the latest input/output plugins. 2.95 and other version in that range are more "bloated" than 5.x lite.
Winamp 5.08d was the final version of winamp that gives you full control over the output plugin you want to use to play back wma files, although any version prior to 5.08e will not play encrypted wma files.
Winamp 5.08e only allows you to use directsound to play wma files, and winamp 5.091 allows you to use either directsound or waveout.
The lite version is indeed a direct continuation of 2.81 (the last real classic version). Winamp 2.9x instroduced video support and media library and is more bloated in that respect.
I would use either v2.81 (plus peters input/output update, which I can provide a link for) or v5.08e lite or v5.091 lite if you want to playback encrypted wma files.