I think the typical set up is usb out to dac, rca from dac to amp. Not sure what you had in mind - where is the pre-amp in your plan.? I assume the audioengine speakers are powered so they have the power amp part. The computer sound card as a pre-amp is not a great idea.
I'm a mac guy so I don't know about software, but the moon 100d dac is nice (I have one), also PS audio makes a good one for about $800.
I'm a mac guy so I don't know about software, but the moon 100d dac is nice (I have one), also PS audio makes a good one for about $800.