If you're going digital, then MediaMonkey is probably the better choice.

Started using Winamp back around 2000. Eventually got a pro license. Now I use a combination of Zune and Winamp. I'll go for Winamp when I want to add vizualizations but stick to Zune otherwise.

To me, creating playlists is a pain. Zune has an function called "smart DJ" that lets you pick a song and create a playlist based on it. Customizable as to how many and whether from your local collection or it can include songs from the Zune service if you have it. I then use a utility called ZPL to convert the playlists to Winamp (not w/Zune Service songs) format and enjoy my visualizations on Winamp. The Zune software doesn't have the equalizer or all the available DSP addons but it has great sound quality (go figure) and the service used to be a great deal when it included 10 free songs (320 cbr) every month for $15 US.

DesktopX Player....duh..

JRiver, hands down the best. Well worth the money.

Are the paid media players way better than the free ones? Or does it just make people feel good buying software?

Basically most of my software are freeebies. I use two media players. Winamp for testing my smx's and Zion for the bells and whistles. (read skins)

I have always used free media players. Iv'e never needed anything over the years that Winamp free has not provided. That being said, my requirements of a media player (for music at least) are very small. If it has reasonable album management and plays music, it's on the list!
(i use VLC for all video requirements)

I have no problem buying software though, but it needs to be something that cannot be done or found any other way.

Is anyone using, or has used Foobar 2000? it was on a recommended list on Cnet. Ive had a look but any feedback would be appreciated.

Foobar is mostly used for FLAC playback, but also is a good mp3  player, very light footprint however, not sure it's still supported. I'd choose this if I used a free player first above all other freeware players.

Yes, I feel good buying software that is worth it and meets my expectations as a consumer...plus I'm supporting furthur development for a quality product. 

Hey, I use what I skin...lol.

It's still in development.....just not very fast track. I believe a new version was released last month.

I've tried it and my only gripe is that it's assembly ware. There are "plugins" for damn near everything you need but you've got to spend the time trying them out and deciding which work best for you and "assembling" your player.

Winamp has Flac support (will rip in Flac) in fact I can't think of any audio format it doesn't support.

MusicBee

I agree with Lantec...not really into hunting down equalizer presets. You're right about it being assembly-ware no doubt. Deviant Art has some really cool skins for it though, my main reason for using it in the past. Glad to hear it's still being updated.

I use iTunes religiously. My only hangup is that you have to correct most ID3 tagging and embed album artwork before you can import the files into iTunes. One perk among many is almost all 1.27 TB of my library is lossless which itunes will down convert to 128 AAC for my iPhone when synced. Doesn't get better then that.

I use spotify, It does a great job combining what music you already have on your system and integrating it with new stuff.
It's light on resources and is probably the best source of free music out there.
It also has no problem opening any downloaded audio file (such as a podcast) and adding it to the library

Free for a time and it is no good for the many facebook haters here.

"A six month free trial period is activated upon initial login with a Facebook account, where a user can listen to an unlimited amount of music supported by visual and radio-style advertising. After the trial, Spotify will make tracks unavailable once they are played 5 times and has a listening limit of ten hours per month.^[14] An "Unlimited" subscription removes advertisements and time limits and a "Premium" subscription introduces extra features such as higher bitrate streaming, offline access to music and mobile app access.^[15] An active Facebook account is required to use Spotify, unless the user has registered for a Spotify-only account before 22 September 2011. Subscriptions are restricted to people with credit/debit cards or PayPal accounts registered in certain countries" Source is from wikipedia. http://en.wikipedia.org/wiki/Spotify

I would certainly agree with you on that. I have been using dfx for years and it makes a huge difference in sound quality. What most people do not know is there is even a program for making your own skins using existing winamp skins. It only works with the classic skins or skins that use bmp images. Here is a skin I made for one of my favorite winamp skins called Frequency. It is the bottom window.

It still does include the 10 free songs. It's also cheaper if you pay quarterly or yearly.