which output setting sounds best?

I won't pursue it further, but your honesty really doesn't help the OP. He's already purchased the gear, and wants a little advice on setup.

Don't presume that your sage advice on how to listen and what to listen for is what's necessary in every instance. My only point was that you weren't offering any real help, just planting a seed of doubt and disgust in the OP's mind that he may have made a bad choice with his hard-earned dollars.

I hope you never need advice on a piece of gear; I'm sure someone with a much more expensive system will be waiting for an opportunity to tell you it's garbage and you shouldn't worry about the minutia.

Ekwisenek, It doesn't matter how much the gear costs - what matters is HOW IT SOUNDS. I appreciate the recommendations I receive on the forum. We are all in different places financially and all have different budgets. The idea is to get the best within your means.

Ditch Vista and go Win7 64 bit if your laptop is less than 2 years old; Vista is badly flawed for audio fidelity. I A/B'd Vista Ultimate 64 bit vs Win7 Home 64 bit and Win7 was much better for fidelity. However the hardware architecture of your laptop will limit you as Cerrot implied. It will do fine if you have a playback system under $1500 but for more expensive systems, Mac options or other designed by intent music server will deliver better what you payed for.

Win 7 combined with Wasapi is the proven winner and yes, you'll hear the difference with your HRT... upgrade when you can and for now, enjoy.

By the way Bob, I don't know if Cerrot has heard a Music Streamer II +, I haven't but I've read a solid 50 different people say that it is a wonderful bang for the buck DAC...

Cerrot, did you hear this or a Music Streamer, Music Streamer Plus, Music Streamer II, Music Streamer II+ or iStreamer or Music Streamer Pro.
From What I read the II+ is head and heals above anything that came before it and is still a very nice upgrade over the standard Music Streamer II.
I've seen it Comared to many $1000 DAC's with good reviews.
I hear Kevin Halverson of Muse fame that created the music streamer product has some nice improvements coming out right now.