Of all the players I've tried throughout the years (closing on 1½ decade), and I've tried -many-, I've found that WinAmp is currently the best and easiest to use for music - and by far the easiest to skin (Classic skins).
It is offcause the player I use, and it's been my main music player since 1998. (I use VLC for video/films)

BUT.... WinAmp's not the best player ever to have seen the light of day.
Two other players could potentionally have knocked WinAmp off of the throne. K-Jöfol and Sonique were by far the better players when they still were in developement. Sadly though, the K-Jöfol team were headhunted over to WinAmp and Sonique was bought by Lycos (The Google of it's days), which was the death for both players.

Why do people say it's hard to edit tags in iTunes? I edit tags quite often with no issues.

Given that I like to listen to one song over and over again in an endless loop and only change it once every 10 minutes or so, I never really had to move beyond YouTube Repeater.

no player handles tags as well as MP3tag LINK

Yep, just a little bit of skinning history there for all.

I still have kJofol somewhere [and my skins for it], but I have always stuck with Winamp [2.9x] ....

My Tagger of choice!

Before the bloatness began.

Winamp used to be the only media player I would use but recently I have been using Xion for music and Media Player Classic for everything else.

That's one reason why I've always spent the little extra money and used the paid pro version. It cleans things up a bit and I gotta tell ya , it sounds amazing on my surround sound system.

What bloatness does winamp have? I also use the paid version but even with the free version you can have only the main player skin with simple buttons and music info. Perhaps the bloatness has to do with size and registry entries but it is not hard on resources on my basic computer. I use iTunes, aimp and xion from time to time but I always go back to winamp pro.

WA 2x was the hey-day of WA and its skinning.....a lot of people started with WA.

Some say v3 was SO BAD they simply skipped v4 and went straight to v5 just to distance themselves from the disaster....

But then....back about that time the CEO called me a 'clusterfuck'....so he got one thing right....

I remember version 4. It was a disaster. Waited for version 5 to come out before going for it again.

Used WinAmp for many, many years.  Now I actually just use Google Music (I think it's been renamed to Google Play or something like that).  Free (obviously) and you can login with your gmail or G+ account.

You'll download a small app which will upload all your MP3's to "the cloud" and then all your music is now available anywhere via Google Music.  Pretty sweet and a good backup actually for all your music.  If your PC crashes you can download all your music from Google Music at anytime.

The actual desktop program I use is foobar2000.  It's simple, and it works well.  That's all I need.

For web playing, I generally go with Audiogalaxy.  Streams from my music collection at home, no need to upload anything.