Starting over

The shanling is way too weak for anything but the most efficient speakers. Going with any of the Music Halls will get a lot more power and you can get a class A amp which will get you a lot of warmth. I've seen them used for $500-700. 50 watts will drive most speakers.

The New Bose Acoustic Wave Music System 2 !

Headphones are the way to go, without a doubt. I like the Sennheiser HD600s ($350) or the HD650s ($450) and the Pro-Ject Headbox SEII ($300) amp. Then get yourself an iPod or a computer with a decent soundcard, anything that gives you a pure output, use lossless music files, and you will be stunned at how good it is.

I also have the N802 and those $350 headphones hold up really well against them.

One way to start over for less than $1000 is to go with the Fatman - iTube - Stereo Integrated Amp w/iPod dock. You get a tube hybrid integrated amp with 13 watts per channel and an iPod dock. Audio Advisor has these on sale for $400 w/o speakers, and $500 with speakers. Add an iPod, a pair of small monitors (if you don't go with the "with speakers" choice that Fatman offers) of your choosing and/or a set of headphones, and you should have a MUCH better than average sounding iPod based system. Down the road when you finances improve, then the Fatman system would make great second system in a bedroom or office enviroment.

I went the heaphone route when I had to get rid of the main rig due to twin boys arriving. Got the Senn 650's and a Mier Audio Corda Aria amp w/ the built in USB DAC. I have to say I have been pretty happy with the it so far. May try going with a tube amp and separate DAC at some point as the sound is a bit thin for my taste but, it does satisfy the craving.

Got the Senn's used for $250 in mint condition.
Bought he Mier new for around retail