Will a $500 dac (scott nixon tubedac, ack! dack, or CI VAC-1) noticeably improve the sound over the internal dac of the squeezebox? I've heard the squeezebox's dac is pretty good, but I am not sure how it compares to the ones I listed.

Can you wait 6 months while saving up $20 a week? Then you will have enough for a Benchmark DAC-1 if you add the $500 you have right now.

My first Squeezebox is coming on Monday, and that's the DAC I have my eye on. My plan is to wait for a while and listen through its analog out (using speakers). Then I will buy a really good DAC when I have the $$$. I've been burned too many times from buying "halfway."

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the amount of time doesn't really matter
he'll still be spending an extra $500

I am not totally against spending a $1000 for a dac if necessary. That is, if one of the $500 dacs I mentioned does not make much of a difference, but a $1000 dac like the dac1 would make a big difference, then I would save up for the dac1. I am always trying to find the point of diminishing returns.

I've heard good things about the dacs I mentioned. Also, two of them are able to be modded if I want to upgrade in the future. I just don't know how they compare in stock form to the dac in the squeezebox. If they are comparable, which I somewhat doubt, then I would simply listen to the squeezebox as is for a year or so, and then when I get the urge, upgrade to a dac that might make have a more noticeable impact (e.g. Dac1).