Well, if I were to rank my players, it would look something like this:
JVC XA-HD500
Kenwood HD20GA7
Creative Zen Touch
Cowon S9
Sansa View
Creative Zen Vision
I leave the iRiver H120 out of comparison since I have left it back in Sweden and did not bring it to Japan where I live during 2010. By the way, the older iRiver players such as H120/140 and H320/340 are seen as their best ones. After those ones, it seems that the sound quality is not as good. I bought a used H120 on Ebay since I had read many reviews about it saying that it was a very good sounding MP3 player.
My ranking might change by mood, but I think not too much.
The JVC and Kenwoods are very rare Japanese DAP:s and they sound great. However, they cannot play lossless files. The Creative Zen Touch is the best Creative player I have heard, but quite old (released in 2004) and it does not play lossless. The Cowon S9 is great and has got a good EQ that you might need to tweak a bit to get the sound to your liking. It took a long while for me, and now I have found a good sound. The presets "Viva", "Viva2" and the three "Headphone" are also good.
I like older MP3 players and I am a bit of a collector of older and more rare models. Now when I am in Japan, I have had the chance of buying an old JVC and an old Kenwood player. They were both released around 2005 and still sound great compared to modern players.
If you could consider MP3 format, I would recommend the JVC and Kenwoods. I saw that there is a JVC for sale here on Head-fi right now. It is a very rare player outside of Japan and it sounds very good with a distinct bass, clear mids and very lush and nice highs. However, it is only 6GB and the gui is a bit old (considering it is 5 years old). I still like mine very much.
People might recommend the Nationite S:flo2 and the HifiMan players. These are Chinese build "audiophile" players. I prefer players built by larger companies - the build quality and quality control of smaller Chinese companies is not always the best. However, you want to use an amp, and I think that both of these have got line outs which the J3 and Clip+ does not.
With your big budget, you could go for a 32GB Cowon J3 AND Sansa Clip+ with a MicroSD card. And you might also have money to try out the JVC on sale here at Head-fi (however it only plays MP3 files).
My advice is to do a bit of searching and find different reviews and not go for the first player you are recommended. Wait until you feel that you've found "the right one".