I've been listening to MP3s on my computer since 1997.  I've never owned an MP3 player for carrying around.  I've always had a CD player in my car and had a CD player to carry around when I was in undergrad, MP3 players were still pretty rare then.  Now that I'm back in school and walking around all the time I'd really like to get one.  Also, I'm heading to NYC this weekend, and the prospect of several hour long bus rides and subway rides leads me to believe the time is right to break down and get one.

So if anyone has any experience to share or any suggestions of models to purchase let me know.  My girlfriend suggested I get an iPod Touch but I don't know if I want to spend $240, and I absolutely do not want to be tied to using iTunes/iStore because I hate the software.  Whatever I get needs to be compatible with Winamp (I'm not sure to what extent iPods are compatible with non-iTunes players?).  Anyways, I'm gonna look up some stuff online.  But personal experiences would help me out a lot.  Let me know.

Get an old model Sansa.

I got my girlfriend the Sansa E280.

It uses microSD cards. 8g is the limit normally, but if you install rockbox on it you can get 8g microSD cards and double your memory to 16g.

Easy interface, durable, and won't dump your entire collection if you drop it like a hard drive player.

Stay away from the Ipod mob. Seriously.

I have an iPod Photo 30gb... its 4 years old now, still works. I generally hate Apple products, and this one has things about it I dont like, but for the most part, it's fine.

I dont much care about iTunes, I do whatever I want with it anyways. I prolly only use 4-5 gig for music, its great as a portable hard drive.

If you want to get music off it (one of the things I really dislike about iPod's), there's software called iDump, which will dump alll songs to a computer.

Picking an MP3 player is a very subjective experience.  What one person likes about a product might turn you off immediately, so it's hard to offer advice.

What I'll do here is point out a specific manufacturer that I like, and then explain the technical merits of their products:  Cowon America.

I've personally used the Cowon D2 player for several years.  When you plug it into your computer, it acts like a regular USB device, so you just move files into place.  It supports a wide range of audio AND video formats, including lossless formats (FLAC) and divx containers.  It also has an FM radio that's good enough to receive radio station broadcasts while in an airplane!  The D2 supports normal-sized SDHC cards out of the box, too, which means that my 4 GB player was upgraded to a 20 GB (4+16) player in about 2 minutes. 

With an integrated lithium ion battery, the D2 gets something like 50+ hours of continuous audio playback (as long as you don't have the volume maxed out).  And it'll recharge off of the USB port, thus if you're like me with a blackberry or similar phone device, you can travel with just one power cord (or none, as long as you don't mind running your computer to charge your appliances).

I ALSO had an iAudio 7 available to me for a little while, but that left in the break-up.  But, while I did have access to it, it was a sweet little music player, with a very interesting interface.  Same tech specs for playback, same awesome battery life.

Make sure to check out Cowon's website above; they have cute little videos posted on how each of their products work; sort of a video unboxing!

You can order these directly from jetmall (Cowon's storefront), and you can also get the newer models on newegg.com or amazon.com.
edit:  the entry-level iAudio 7 is $100 @ jetmall, the entry-level D2 is $110.

I found a newer gen Nano on the street in Annapolis last year. I don't use iTunes, but i don't like the fact that I can't charge it or just change the battery anytime. I'd love to get a 2-4G MP3 player that just uses AAA batteries for hiking. But I can't find one.

I had (have? it may not be lost, possibly just misplaced) an iPod, and frankly they suck. I use iTunes as my MP3 player on my comp, and I quite like a lot about it, but the fact that iPods are such bitches about being able to add or remove MP3s on multiple computers turns me right off. Also, the battery life sucks. If I ever get another MP3 player, I'll get something more like what Luke was talking about.

Get a Shu-misa.  The new models rock.

my next cell will hold 4 gigs of music, a 6 megapixel camera, have a qwerty keyboard, be connected to exchange and will play Nintendo DS games.

The government will be able to track me on it, they will know that I'm playing bubble bobble

Please dont get me started on megapixels and sensor size.

check the senor size if its small, megapixels dont mean sfa.

dude, this is Japan. All gadgetry is created awesome

Show me a dildo with an mp3 player and a decent sized cam sensor and I will concede defeat.

Where are those dildos with the cameras on the end sold?

in Japan in November

You should show up drug, we might need somebody to test it for us.

Mail it, I'll do it from here and post the footage.

my next cell will hold 4 gigs of music, a 6 megapixel camera, have a qwerty keyboard, be connected to exchange and will play Nintendo DS games.

The government will be able to track me on it, they will know that I'm playing bubble bobble

You'll be fine, they know terrorists would never play bubble bobble.

my next cell will hold 4 gigs of music, a 6 megapixel camera, have a qwerty keyboard, be connected to exchange and will play Nintendo DS games.

The government will be able to track me on it, they will know that I'm playing bubble bobble

So you going for the 386 or 486 laptop?

Show me a dildo with an mp3 player and a decent sized cam sensor and I will concede defeat.

iVibe!

Tandy!

Tandy is still going???

Is it still way overpriced chinese made donkey shit?

Haha, no way dude.  They stopped making computers in 1991.

But the stores still exist, no?

No fucking clue.  All I remember is playing Ports Of Call, The Incredible Machine, and Apogee games on my friends Tandy.  Fucking killer games.

I found a newer gen Nano on the street in Annapolis last year. I don't use iTunes, but i don't like the fact that I can't charge it or just change the battery anytime. I'd love to get a 2-4G MP3 player that just uses AAA batteries for hiking. But I can't find one.

Wal-Mart used to sell lots of mp3 players that ran off of AAA's.  My nephew had one.  It was simplistic and low-quality, but it played the songs well enough.

I have one of those around here somewhere.

I'm sure a barter can be arranged.

Whatcha need, bro?

The government will be able to track me on it, they will know that I'm playing bubble bobble

As in Bubble Bobble Plus for Wii? I hear that just came out.

No fucking clue.  All I remember is playing Ports Of Call, The Incredible Machine, and Apogee games on my friends Tandy.  Fucking killer games.

The apogee family was fucking sweet.

Whatcha need, bro?

Let me find it, then send me 15 bucks worth of assorted junk.

I can make this happen.

Found it.

You wanna exchange mail addys, hit up my pm box.