I currently have a 3rd gen 20GB iPod (the dock connector one) and it's been a pain in my ass ever since I got it. I'm looking for a replacement and was hoping for a point in the right direction.

I'm looking for the following features:

1.) HD Storage of at least 20-40GB. Going to need a HD based player to meet this need, so no flash players please.
2.) Support for as many codecs as possible. I have my entire music library stored in FLAC lossless format and I want to be able to convert my music to multiple formats and still have the player support them.
3.) No proprietary program that must be used to manage the media on the device. iTunes blows...
4.) General ease of use: quick plug and play access to the computer via USB or Firewire
5.) Gapless playback
6.) Best sound quality possible in a reasonable price range (price range listed below)
7.) Playlist support and easy navigation when using the device
8.) $200-$300 price range

Absolutely done with iPods...You could give me a free one and I would just give it to my girlfriend at this point...

I was looking at the iRiver's and was impressed but I read several reviews of the H340 that mentioned low battery life and a generally low life span for the device. Also, have they released anything new recently?

I'm not a fan of Sony at all, so I will most likely stay away from their products. I also hear lots of people who use their players complaining about the software that comes with the devices. Also, are they still trying to push ATRAC on people? WTF...

Any suggestions would be greatly appreciated!
JXL

You might consider the iAudio X5[L], which you can find more information about here: http://www.cowonamerica.com/products/iaudio/x5/. I own the X5L 30GB model, bought it for about $280 on Amazon a few months ago.

I'm quite pleased with the device overall. The original firmware is pretty ugly though, so I installed Rockbox, which can pretty much do anything you want (inc. gapless).

Rockbox software is what you need. Only a certain number of players are suppored. That ticks of everything but your first and last requirements. The ihp-140 which I have would suit you but you'd have to get a used one. Some ipods work with rockbox too.

Toshiba Gigabeat F/X or iRiver H340, either way running Rockbox.

You're basically the stereotypical Rockbox user. Might as well embrace it now.

Great bonus is that rockbox is free, you have lost nothing, can buy another player if it doesnt work out

If you want flac or ogg vorbis the cowon's are the way to go but i have the creative zen vision M in white and i love it. I've had an ipod before and it's a great change. It's about $230 on amazon i got it off of zipsoomfly for $180 for christmas rebate. It doesn't have Gapless playback as far as i know but it's a kickass player

Seriously. Rockbox.

You can even try it out on your iPod 3G. Though I believe only Musepack is the only lossy codec that is realtime on that target. On the plus side, Wavpack and FLAC apparently work fine.

another vote of confidence in cowon's products here - I have bought an mp3 and 2 pmp's from them - superb products.

You definitely want a Rockboxable player.
The iRiver H1xx and H3xx series players are very mature and stable with Rockbox, but the downside is you will be buying used, and will be paying for their (excellent) recording capabilities, regardless of if you value it or not. You can easily achieve more than 20 hours of runtime with an inexpensive replacement battery.

The Cowon iAudio X5 is also a mature Rockbox target, with good runtimes, and you can buy one new. The X5L has even better runtimes but is a single-platter hard drive, limiting you to 30GB stock, 40GB with a replacement drive currently.

The Toshiba Gigabeat F/X series of players are the new kids on the Rockbox block. Expect 15 hours of runtime with the stock battery. They are inexpensive on eBay (new or used), and have a monster of a CPU. They are at least as stable as the coldfire targets (H100, H300, X5) and have enough CPU to run every DSP under the sun w/o skipping or battery life degradation.
You can find them in 10, 20, 40, and 60GB varieties for well under $200.
They also will win in the eye-candy department.
Unlike the three players above, though, there is no recording and no FM radio.

Thanks for all of the info. It saved me a ton of time when I got a few minutes to look around today. With a one year old baby, a demanding job, and a GF my free time is all but gone...so I appreciate it.

I checked out the Rockbox pages and my iPod 3G is not fully supported. It says that it will work but with very poor performance. It also has a post from back in July of '06 saying that the work is still in progress. Guess I'll just have to get a new player to test it out.

I researched the Cowon iAudio X5 and was extremely impressed. It has native FLAC & OGG support and a large amount of solid reviews from its users. Even without the Rockbox firmware I would be very interested in it. It fits my price range perfectly and it has enough space for just about whatever I would want to use; lossless audio formats or vids or whatever. I would need to load Rockbox to get the gapless playback, but besides the gapless it meets every requirement I had listed already. Very impressed!
Amazon: Cowon iAudio X5 60GB
Cowon iAudio X5 Specs

The Toshiba Gigabeat MES60VK 60GB also looks like a winner. It costs a little less than the iAudio ($50 or so less) and it looks a little sleeker (Nicer looking screen and a little flashier design). The reviews are somewhat lackluster though...Several users discussing problems transfering audio and video to the device and problems keeping the media on the device once it was loaded. I was also reading on the rockbox page and the latest Gigabeat (the S series) isn't supported yet. It looks very promising but I'm not fully sure it's mature enough for me yet.

I'll be getting my yearly bonus this Friday and will most likely get the iAudio X5 60GB, unless something else catches my eye beforehand.

Thanks again for all of the help!
JXL

Well, the F/X and S are different players. The S is not mature enough in the sense that its not supported. However, that doesn't saying anything about the maturity of the F and X series.